CH388978A - Verfahren zur Herstellung von 2,2-Dibenzyl-äthylaminen - Google Patents

Verfahren zur Herstellung von 2,2-Dibenzyl-äthylaminen

Info

Publication number: CH388978A
Authority: CH; Switzerland
Prior art keywords: dichlorobenzyl; bis; acid; chlorobenzyl; melting point
Prior art date: 1959-11-27

Application number

CH1322660A

Other languages

German (de)

English (en)

Inventor

Schorr Manfred

Fussgaenger Rudolf

Nesemann Georg

Bauer Fritz

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1959-11-27

Filing date

1960-11-25

Publication date

1965-03-15

1960-11-25 Application filed by Hoechst Ag filed Critical Hoechst Ag

1965-03-15 Publication of CH388978A publication Critical patent/CH388978A/de

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 8
OUGPXHYMXCVURU-UHFFFAOYSA-N 2-benzyl-3-phenylpropan-1-amine Chemical class C=1C=CC=CC=1CC(CN)CC1=CC=CC=C1 OUGPXHYMXCVURU-UHFFFAOYSA-N 0.000 title description 2
150000003839 salts Chemical class 0.000 claims description 24
150000001412 amines Chemical class 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
150000002825 nitriles Chemical class 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
-1 2,4-dichlorobenzyl Chemical group 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
238000002844 melting Methods 0.000 description 29
230000008018 melting Effects 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
239000000155 melt Substances 0.000 description 20
238000001953 recrystallisation Methods 0.000 description 20
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 19
239000000047 product Substances 0.000 description 18
239000007858 starting material Substances 0.000 description 17
239000003054 catalyst Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
150000001875 compounds Chemical class 0.000 description 14
239000007868 Raney catalyst Substances 0.000 description 13
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 13
229910000564 Raney nickel Inorganic materials 0.000 description 13
230000001476 alcoholic effect Effects 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
238000001816 cooling Methods 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
238000004821 distillation Methods 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000000126 substance Substances 0.000 description 6
YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
MVDWJSYJWKQJEA-UHFFFAOYSA-N (4-chlorophenyl)methyl 2-cyanoacetate Chemical compound ClC1=CC=C(COC(=O)CC#N)C=C1 MVDWJSYJWKQJEA-UHFFFAOYSA-N 0.000 description 4
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
230000003385 bacteriostatic effect Effects 0.000 description 4
239000002585 base Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 4
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FRSIGXBOJCWAJP-UHFFFAOYSA-N (3,4-dichlorophenyl)methyl 2-cyanoacetate Chemical compound ClC1=CC=C(COC(=O)CC#N)C=C1Cl FRSIGXBOJCWAJP-UHFFFAOYSA-N 0.000 description 3
PUVVYQAJJXXUAB-UHFFFAOYSA-N (3,4-dichlorophenyl)methyl propanoate Chemical compound CCC(=O)OCC1=CC=C(Cl)C(Cl)=C1 PUVVYQAJJXXUAB-UHFFFAOYSA-N 0.000 description 3
FOHJFUOCIPECGU-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]pentanenitrile Chemical compound ClC=1C=C(CC(C#N)CCC)C=CC=1Cl FOHJFUOCIPECGU-UHFFFAOYSA-N 0.000 description 3
FOBXJUZVIFQJHW-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-methylpropanenitrile Chemical compound N#CC(C)CC1=CC=C(Cl)C=C1 FOBXJUZVIFQJHW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
238000009835 boiling Methods 0.000 description 3
ATQGYOCVSCTYMO-UHFFFAOYSA-N butyl 2-cyano-3-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methyl]propanoate Chemical compound C(CCC)OC(C(C#N)(CC1=C(C=C(C=C1)Cl)Cl)CC1=C(C=C(C=C1)Cl)Cl)=O ATQGYOCVSCTYMO-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
OGPORIQYBPIXJA-UHFFFAOYSA-N ethyl 2-cyano-3-(3,4-dichlorophenyl)-2-[(3,4-dichlorophenyl)methyl]propanoate Chemical compound C(C)OC(C(C#N)(CC1=CC(=C(C=C1)Cl)Cl)CC1=CC(=C(C=C1)Cl)Cl)=O OGPORIQYBPIXJA-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000012458 free base Substances 0.000 description 3
230000001408 fungistatic effect Effects 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
238000010907 mechanical stirring Methods 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000000967 suction filtration Methods 0.000 description 3
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
ZJNTZYXIJJSRIH-UHFFFAOYSA-N 2,2-bis[(3,4-dichlorophenyl)methyl]pentan-1-amine Chemical compound ClC=1C=C(CC(CN)(CCC)CC2=CC(=C(C=C2)Cl)Cl)C=CC1Cl ZJNTZYXIJJSRIH-UHFFFAOYSA-N 0.000 description 2
QVKDXNNJPIPKTE-UHFFFAOYSA-N 2-cyano-3-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methyl]propanoic acid Chemical compound ClC1=C(CC(C(=O)O)(C#N)CC2=C(C=C(C=C2)Cl)Cl)C=CC(=C1)Cl QVKDXNNJPIPKTE-UHFFFAOYSA-N 0.000 description 2
IQAGANRKNVLBFG-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-[(4-chlorophenyl)methyl]-2-cyanopropanoic acid Chemical compound ClC1=CC=C(CC(C(=O)O)(C#N)CC2=CC=C(C=C2)Cl)C=C1 IQAGANRKNVLBFG-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
QPRBTNAVUPKCIP-UHFFFAOYSA-N Cl.ClC1=CC=C(C=C1)C(C(C)N)C1=CC=C(C=C1)Cl Chemical compound Cl.ClC1=CC=C(C=C1)C(C(C)N)C1=CC=C(C=C1)Cl QPRBTNAVUPKCIP-UHFFFAOYSA-N 0.000 description 2
QXLREMXUDNTVCU-UHFFFAOYSA-N ClC=1C=C(CC(C(=O)O)(C#N)CC2=CC(=C(C=C2)Cl)Cl)C=CC=1Cl Chemical compound ClC=1C=C(CC(C(=O)O)(C#N)CC2=CC(=C(C=C2)Cl)Cl)C=CC=1Cl QXLREMXUDNTVCU-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
NARCWNHYWHVFKD-UHFFFAOYSA-N butyl 3-(2,4-dichlorophenyl)-2-methylpropanoate Chemical compound C(CCC)OC(C(C)CC1=C(C=C(C=C1)Cl)Cl)=O NARCWNHYWHVFKD-UHFFFAOYSA-N 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000000645 desinfectant Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002012 dioxanes Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
235000015110 jellies Nutrition 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
IKPIAUWSINBJMY-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)-2-methylpropanoate Chemical compound COC(=O)C(C)CC1=CC=C(Cl)C=C1 IKPIAUWSINBJMY-UHFFFAOYSA-N 0.000 description 2
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 2
239000004570 mortar (masonry) Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
238000013207 serial dilution Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 1
QOFSAGWVGMXEEY-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-methylpropanenitrile Chemical compound N#CC(C)CC1=CC=C(Cl)C(Cl)=C1 QOFSAGWVGMXEEY-UHFFFAOYSA-N 0.000 description 1
LGWFQRXQEDZFHW-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-cyanopropanoic acid Chemical compound OC(=O)C(C#N)CC1=CC=C(Cl)C=C1 LGWFQRXQEDZFHW-UHFFFAOYSA-N 0.000 description 1
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
RUFKFPUAJHJIRE-UHFFFAOYSA-N Cl.ClC=1C=C(CC(CN)(CCC)CC2=CC(=C(C=C2)Cl)Cl)C=CC1Cl Chemical compound Cl.ClC=1C=C(CC(CN)(CCC)CC2=CC(=C(C=C2)Cl)Cl)C=CC1Cl RUFKFPUAJHJIRE-UHFFFAOYSA-N 0.000 description 1
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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108010010803 Gelatin Proteins 0.000 description 1
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241001123663 Penicillium expansum Species 0.000 description 1
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239000002202 Polyethylene glycol Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241001467018 Typhis Species 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229960005261 aspartic acid Drugs 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
DJACTCNGCHPGOI-UHFFFAOYSA-N butyl 2-cyanoacetate Chemical compound CCCCOC(=O)CC#N DJACTCNGCHPGOI-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229960002598 fumaric acid Drugs 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008274 jelly Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098895 maleic acid Drugs 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940099690 malic acid Drugs 0.000 description 1
HMMNGPVTQGPBTR-UHFFFAOYSA-N methyl 2-cyano-3-(3,4-dichlorophenyl)-2-[(3,4-dichlorophenyl)methyl]propanoate Chemical compound COC(C(C#N)(CC1=CC(=C(C=C1)Cl)Cl)CC1=CC(=C(C=C1)Cl)Cl)=O HMMNGPVTQGPBTR-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
244000005700 microbiome Species 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
208000006379 syphilis Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
239000012085 test solution Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1322660A 1959-11-27 1960-11-25 Verfahren zur Herstellung von 2,2-Dibenzyl-äthylaminen CH388978A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF29941A DE1110171B (de)	1959-11-27	1959-11-27	Verfahren zur Herstellung substituierter Amine

Publications (1)

Publication Number	Publication Date
CH388978A true CH388978A (de)	1965-03-15

Family

ID=7093529

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1322660A CH388978A (de)	1959-11-27	1960-11-25	Verfahren zur Herstellung von 2,2-Dibenzyl-äthylaminen

Country Status (4)

Country	Link
BE (1)	BE597572A (fr)
CH (1)	CH388978A (fr)
DE (1)	DE1110171B (fr)
GB (1)	GB938732A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1292461B (de) *	1965-05-31	1969-04-10	Behr Thomson Dehnstoffregler	Thermostatisches Ventil
DE19933421A1 (de) *	1999-07-16	2001-01-25	Gruenenthal Gmbh	2-Benzyl-3-dimethylamino-1-phenyl-propanderi- vate

1959
- 1959-11-27 DE DEF29941A patent/DE1110171B/de active Pending
1960
- 1960-11-25 CH CH1322660A patent/CH388978A/de unknown
- 1960-11-28 GB GB40880/60A patent/GB938732A/en not_active Expired
- 1960-11-28 BE BE597572A patent/BE597572A/fr unknown

Also Published As

Publication number	Publication date
BE597572A (fr)	1961-05-29
GB938732A (en)	1963-10-02
DE1110171B (de)	1961-07-06

Publication	Publication Date	Title
DE2025961B2 (de)	1973-12-06	Verfahren zur Herstellung von N-(l,l-Dialkyl-3-chloracetonyl)-benzamiden und Derivate von N-(l,l-Dimethyl-3-chloracetonyl)-benzamid
CH344404A (de)	1960-02-15	Verfahren zur Herstellung von neuen Biguaniden
CH373397A (de)	1963-11-30	Verfahren zur Herstellung symmetrischer Diamine
CH388978A (de)	1965-03-15	Verfahren zur Herstellung von 2,2-Dibenzyl-äthylaminen
AT220614B (de)	1962-04-10	Verfahren zur Herstellung neuer substituierter Amine und ihrer Salze
DD151448A5 (de)	1981-10-21	Verfahren zur herstellung von benzothiazolderivaten
DE2354931C2 (de)	1983-12-08	trans-2-Phenylbicyclooctan-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
AT214426B (de)	1961-04-10	Verfahren zur Herstellung von neuen substituierten 3,3,3-Triphenylpropylaminen und deren Säureadditionssalzen
CH356121A (de)	1961-08-15	Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren
CH369759A (de)	1963-06-15	Verfahren zur Herstellung von N-Alkylpiperidin-a-carbonsäureaniliden
CH616406A5 (en)	1980-03-31	Process for the preparation of novel oxime derivatives
CH382181A (de)	1964-09-30	Verfahren zur Herstellung neuer substituierter 3,3,3-Triphenylpropylamine
DE2931255C2 (fr)	1993-05-13
DE833818C (de)	1952-03-13	Verfahren zur Herstellung von neuen mono- und diquartaeren Salzen von Pyrimidylaminocinnolinen
AT204048B (de)	1959-06-25	Verfahren zur Herstellung von neuen Phenazinderivaten
DE869204C (de)	1953-03-05	Verfahren zur Herstellung von Diphenylmethan-4, 4'-diacetonitril
AT165069B (de)	1950-01-10	Verfahren zur Herstellung neuer Phenoxyacetamidine
AT235279B (de)	1964-08-25	Verfahren zur Herstellung neuer 5-Nitrofurfuryliden-hydrazine
DE1074047B (de)	1960-01-28	Verfahren zur Herstellung von Chinazolmen
AT233313B (de)	1964-05-11	Verfahren zur Bekämpfung der Parasiten von Pflanzenorganismen
AT360007B (de)	1980-12-10	Verfahren zur herstellung von 2-(phenylamino)- imidazolin-(2)derivaten und deren salzen
AT210404B (de)	1960-08-10	Verfahren zur Herstellung von neuen substituierten 2, 3-Diphenyl-propylaminen und deren Säureadditionssalzen
DE1768505B2 (de)	1973-10-11	Phenathylaminverbindungen und Ver fahren zu ihrer Herstellung
AT269172B (de)	1969-03-10	Verfahren zur Herstellung von neuen basisch substituierten Alkylxanthinderivaten
DE2017023A1 (de)	1970-10-15	Nitroimidazolyl-nitrone