CH387633A - Verfahren zur Herstellung von 1,2,3,4-Tetrahydroisochinolinen - Google Patents

Verfahren zur Herstellung von 1,2,3,4-Tetrahydroisochinolinen

Info

Publication number: CH387633A
Authority: CH; Switzerland
Prior art keywords: acid; methanol; melting point; isoquinoline; base
Prior art date: 1959-12-09

Application number

CH8161459A

Other languages

German (de)

English (en)

Inventor

Arnold Dr Brossi

Otto Dr Schnider

Max Dr Walter

Original Assignee

Hoffmann La Roche

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.)

1959-12-09

Filing date

1959-12-09

Publication date

1965-02-15

1959-12-09 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1959-12-09 Priority to CH8161459A priority Critical patent/CH387633A/de

1960-08-30 Priority to BE594576A priority patent/BE594576A/fr

1960-08-30 Priority to ES0260703A priority patent/ES260703A1/es

1964-12-26 Priority to OA51043A priority patent/OA00948A/fr

1965-02-15 Publication of CH387633A publication Critical patent/CH387633A/de

Links

238000000034 method Methods 0.000 title claims description 15
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 4
239000002253 acid Substances 0.000 claims description 12
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 claims description 10
150000001408 amides Chemical class 0.000 claims description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
239000008096 xylene Substances 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
150000003526 tetrahydroisoquinolines Chemical class 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
BQNOIPNXSHVKPI-UHFFFAOYSA-N 1-(1-phenylethyl)-3,4-dihydroisoquinoline Chemical compound N=1CCC2=CC=CC=C2C=1C(C)C1=CC=CC=C1 BQNOIPNXSHVKPI-UHFFFAOYSA-N 0.000 claims description 2
CLSQMTNDUXCOND-UHFFFAOYSA-N C1(=CC=CC=C1)C(C)C1N(CCC2=CC=CC=C12)C Chemical class C1(=CC=CC=C1)C(C)C1N(CCC2=CC=CC=C12)C CLSQMTNDUXCOND-UHFFFAOYSA-N 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
239000002585 base Substances 0.000 description 24
238000002844 melting Methods 0.000 description 21
230000008018 melting Effects 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
-1 halogenated benzene aldehyde Chemical class 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
238000007069 methylation reaction Methods 0.000 description 7
229940095064 tartrate Drugs 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 4
ALKOLYNQANQTPH-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenyl)ethyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline Chemical compound ClC=1C=C(C=CC1Cl)CCC1N(CCC2=CC(=C(C=C12)OC)OC)C ALKOLYNQANQTPH-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229960001270 d- tartaric acid Drugs 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
230000009435 amidation Effects 0.000 description 3
238000007112 amidation reaction Methods 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 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
238000001816 cooling Methods 0.000 description 3
NTBIYBAYFBNTCD-UHFFFAOYSA-N dibenzoyl 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-UHFFFAOYSA-N 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
239000000155 melt Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
BBSLOKZINKEUCR-UHFFFAOYSA-N 3-(4-chlorophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(Cl)C=C1 BBSLOKZINKEUCR-UHFFFAOYSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical class OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
229910052500 inorganic mineral Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000011987 methylation Effects 0.000 description 2
239000011707 mineral Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000000926 separation method Methods 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
IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JIOZLMQZYORGDP-UHFFFAOYSA-N 1-(1-phenylethyl)-1,2,3,4-tetrahydroisoquinoline Chemical class N1CCC2=CC=CC=C2C1C(C)C1=CC=CC=C1 JIOZLMQZYORGDP-UHFFFAOYSA-N 0.000 description 1
KRAKKHKATGRHFQ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenyl)ethyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride Chemical compound Cl.ClC=1C=C(C=CC1Cl)CCC1NCCC2=CC(=C(C=C12)OC)OC KRAKKHKATGRHFQ-UHFFFAOYSA-N 0.000 description 1
FPANOAGJIXLUKT-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CCC1=CC=C(Cl)C=C1 FPANOAGJIXLUKT-UHFFFAOYSA-N 0.000 description 1
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 description 1
KYXSVGVQGFPNRQ-UHFFFAOYSA-N 2-methyl-3,4-dihydro-1h-isoquinoline Chemical class C1=CC=C2CN(C)CCC2=C1 KYXSVGVQGFPNRQ-UHFFFAOYSA-N 0.000 description 1
ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000723346 Cinnamomum camphora Species 0.000 description 1
FCEUIICLXRFREI-UHFFFAOYSA-N Cl.ClC1=CC=C(C=C1)CCC1NCCC2=CC(=C(C=C12)OC)OC Chemical class Cl.ClC1=CC=C(C=C1)CCC1NCCC2=CC(=C(C=C12)OC)OC FCEUIICLXRFREI-UHFFFAOYSA-N 0.000 description 1
JDAHWBJPNFSEJY-UHFFFAOYSA-N Cl.FC1=CC=C(C=C1)CCC1NCCC2=CC(=C(C=C12)OC)OC Chemical compound Cl.FC1=CC=C(C=C1)CCC1NCCC2=CC(=C(C=C12)OC)OC JDAHWBJPNFSEJY-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XDHURRKRWNJJPJ-UHFFFAOYSA-N FC1=CC=C(CCC2N(CCC3=CC(=C(C=C23)OC)OC)C)C=C1 Chemical compound FC1=CC=C(CCC2N(CCC3=CC(=C(C=C23)OC)OC)C)C=C1 XDHURRKRWNJJPJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 1
241001026509 Kata Species 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
MIOPJNTWMNEORI-OMNKOJBGSA-N [(4s)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-OMNKOJBGSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 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
230000000202 analgesic effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229960000846 camphor Drugs 0.000 description 1
229930008380 camphor Natural products 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 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
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
YBCPYHQFUMNOJG-UHFFFAOYSA-N metofoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C)C1CCC1=CC=C(Cl)C=C1 YBCPYHQFUMNOJG-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 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
238000010899 nucleation Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH8161459A 1959-12-09 1959-12-09 Verfahren zur Herstellung von 1,2,3,4-Tetrahydroisochinolinen CH387633A (de)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CH8161459A CH387633A (de)	1959-12-09	1959-12-09	Verfahren zur Herstellung von 1,2,3,4-Tetrahydroisochinolinen
BE594576A BE594576A (fr)	1959-12-09	1960-08-30	Procédé pour la preparation de dérivés de tetrahydroisoquinoleine
ES0260703A ES260703A1 (es)	1959-12-09	1960-08-30	Procedimiento para la fabricaciën de derivados de tetrahidroisoquinolina
OA51043A OA00948A (fr)	1959-12-09	1964-12-26	Procédé pour la préparation de dérivés de tétrahydroisoquinoléine.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH8161459A CH387633A (de)	1959-12-09	1959-12-09	Verfahren zur Herstellung von 1,2,3,4-Tetrahydroisochinolinen

Publications (1)

Publication Number	Publication Date
CH387633A true CH387633A (de)	1965-02-15

Family

ID=4538969

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH8161459A CH387633A (de)	1959-12-09	1959-12-09	Verfahren zur Herstellung von 1,2,3,4-Tetrahydroisochinolinen

Country Status (4)

Country	Link
BE (1)	BE594576A (fr)
CH (1)	CH387633A (fr)
ES (1)	ES260703A1 (fr)
OA (1)	OA00948A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3415526A (en) *	1967-05-29	1968-12-10	Jack S. Wiener	Sound emitting device

1959
- 1959-12-09 CH CH8161459A patent/CH387633A/de unknown
1960
- 1960-08-30 BE BE594576A patent/BE594576A/fr unknown
- 1960-08-30 ES ES0260703A patent/ES260703A1/es not_active Expired
1964
- 1964-12-26 OA OA51043A patent/OA00948A/fr unknown

Also Published As

Publication number	Publication date
OA00948A (fr)	1968-03-22
BE594576A (fr)	1961-07-28
ES260703A1 (es)	1961-03-01

Publication	Publication Date	Title
EP0241003B1 (fr)	1993-10-06	Dérivés de 4H-1-benzopyran-4-one, procédé pour leur préparation et leur utilisation comme médicaments
EP0110372B1 (fr)	1986-09-10	Dérivés de la 1-phénylisoquinoléine, procédé pour leur préparation, compositions pharmaceutiques contenant ces composés et leur utilisation
DE2404113A1 (de)	1974-08-08	4-phenylpiperidine und ihre salze mit pharmazeutisch annehmbaren saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH621115A5 (fr)	1981-01-15
DE2229695A1 (de)	1974-01-31	2-(heteroaryl-methyl)-5,9 beta-dialkyl6,7-benzomorphane, deren saeureadditionssalze sowie verfahren zu deren herstellung
DE2411382A1 (de)	1975-09-18	Neue 2-tetrahydrofurfuryl-6,7-benzomorphane, deren saeureadditionssalze, ihre verwendung als arzneimittel und verfahren zu deren herstellung
DE2105743A1 (en)	1972-08-31	2-(furylmethyl)-6,7-benzomorphans - useful as cns active agents
DD149071A5 (de)	1981-06-24	Herstellung 2-substituierter trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole
DE1620198B2 (de)	1974-09-19	5H-Benz eckige Klammer auf f eckige Klammer zu 2,5-oxazocine oder Benz eckige Klammer auf g eckige Klammer zu 2,6-oxazonine, ihre Salze und Arzneimittel
DE899354C (de)	1953-12-10	Verfahren zur Herstellung von Morphinanabkoemmlingen und ihren Salzen
CH639639A5 (en)	1983-11-30	Alpha-fluoromethyl-alpha-amino-alkanoic acids and their esters
US2355659A (en)	1944-08-15	Piperidine derivatives and process for the manufacture of the same
EP0064685A1 (fr)	1982-11-17	Dibenzo(de,g)quinolines, leurs procédés de préparation et les médicaments les contenant
CH387633A (de)	1965-02-15	Verfahren zur Herstellung von 1,2,3,4-Tetrahydroisochinolinen
AT219041B (de)	1962-01-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
EP0000013B1 (fr)	1980-10-15	4-Phényl-8-amino-tetrahydroisoquinoléines, compositions pharmaceutiques les contenant et procédé pour préparer ces compositions
DE2217420A1 (de)	1973-10-31	N-thienylmethyl-heterocyclen, deren saeureadditionssalze sowie verfahren zu deren herstellung
DE1014545B (de)	1957-08-29	Verfahren zur Herstellung von N-Alkyl-, N-Alkenyl- oder N-Aralkyl-3-oxymorphinanen
US3127405A (en)	1964-03-31	I-phenylalkyl
CH460773A (de)	1968-08-15	Verfahren zur Herstellung von substituierten 3-(3-Hydroxyphenyl)-1-phenacyl-piperidinen
AT256111B (de)	1967-08-10	Verfahren zur Herstellung der razemischen und der (+)-Form des neuen 1-(2',4',5'-Trichlor-phenäthyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisochinolins und deren Säureadditionssalze
AT212832B (de)	1961-01-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
AT200265B (de)	1958-10-25	Verfahren zur Herstellung von dl-Emetin
AT206441B (de)	1959-11-25	Verfahren zur Herstellung von substituierten 2-Hydroxy-1,2,3,4,6,7-hexahydro-11 bH-benzo[a]chinolizinen
DE939207C (de)	1956-02-16	Verfahren zur Herstellung von als Lokalanaesthetica verwendbaren basisch substituierten Fettsaeure-(2-chlor-6-methyl-aniliden) und ihren Salzen