CA1047035A - 1-(amino-alkyl)-2-aryl-cyclohexane alcohols and esters - Google Patents

1-(amino-alkyl)-2-aryl-cyclohexane alcohols and esters

Info

Publication number: CA1047035A
Authority: CA; Canada
Prior art keywords: phenyl; methyl; formula; ethyl; dimethylamino
Prior art date: 1974-03-04
Legal status (The legal status 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 status listed.): Expired

Application number

CA221,132A

Other languages

English (en)

French (fr)

Other versions

CA221132S (en

Inventor

Bola V. Shetty

Telfer L. Thomas

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pennwalt Corp

Original Assignee

Pennwalt Corp

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.)

1974-03-04

Filing date

1975-03-03

Publication date

1979-01-23

1975-03-03 Application filed by Pennwalt Corp filed Critical Pennwalt Corp

1979-01-23 Application granted granted Critical

1979-01-23 Publication of CA1047035A publication Critical patent/CA1047035A/en

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title claims abstract description 15
238000000034 method Methods 0.000 claims abstract description 87
230000008569 process Effects 0.000 claims abstract description 47
150000001875 compounds Chemical class 0.000 claims abstract description 36
239000002253 acid Substances 0.000 claims abstract description 31
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 25
150000003839 salts Chemical group 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
230000003287 optical effect Effects 0.000 claims abstract description 11
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000001589 carboacyl group Chemical group 0.000 claims abstract description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
-1 4-phenyl-piperazino radical Chemical class 0.000 claims description 85
238000002360 preparation method Methods 0.000 claims description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 28
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 26
239000012346 acetyl chloride Substances 0.000 claims description 23
ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims description 23
239000012280 lithium aluminium hydride Substances 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 19
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
POPDOWPKMHATOS-UHFFFAOYSA-N 1-[1-(dimethylamino)propan-2-yl]-2-phenylcyclohexan-1-ol Chemical compound CN(C)CC(C)C1(O)CCCCC1C1=CC=CC=C1 POPDOWPKMHATOS-UHFFFAOYSA-N 0.000 claims description 13
DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 claims description 13
230000002829 reductive effect Effects 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
VKNQPZKJCJNZCT-UHFFFAOYSA-N 2-(1-hydroxy-2-phenylcyclohexyl)propanoic acid Chemical compound OC(=O)C(C)C1(O)CCCCC1C1=CC=CC=C1 VKNQPZKJCJNZCT-UHFFFAOYSA-N 0.000 claims description 10
VMQWZQQMFQFNSY-UHFFFAOYSA-N 1-[1-(dimethylamino)propan-2-yl]-2-(4-methoxyphenyl)cyclohexan-1-ol Chemical compound C1=CC(OC)=CC=C1C1C(C(C)CN(C)C)(O)CCCC1 VMQWZQQMFQFNSY-UHFFFAOYSA-N 0.000 claims description 9
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 claims description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 9
JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
239000012458 free base Substances 0.000 claims description 6
TVQPXLMQOZWEBA-UHFFFAOYSA-N nexeridine Chemical compound CN(C)CC(C)C1(OC(C)=O)CCCCC1C1=CC=CC=C1 TVQPXLMQOZWEBA-UHFFFAOYSA-N 0.000 claims description 6
150000002825 nitriles Chemical class 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 5
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
BNMKGJXJUUMGNL-UHFFFAOYSA-N 1-(1-aminoethyl)-2-phenylcyclohexan-1-ol;hydrochloride Chemical compound Cl.CC(N)C1(O)CCCCC1C1=CC=CC=C1 BNMKGJXJUUMGNL-UHFFFAOYSA-N 0.000 claims description 3
KZFKFDSWAGMTTK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)cyclohexan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C1C(=O)CCCC1 KZFKFDSWAGMTTK-UHFFFAOYSA-N 0.000 claims description 3
BPWLFLLZEYWGAV-UHFFFAOYSA-N [2-(3,4-dimethoxyphenyl)-1-[1-(dimethylamino)propan-2-yl]cyclohexyl] acetate;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1C1C(C(C)CN(C)C)(OC(C)=O)CCCC1 BPWLFLLZEYWGAV-UHFFFAOYSA-N 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
YBEZEXWSGXVVIJ-UHFFFAOYSA-N 1-[1-(dimethylamino)propan-2-yl]-2-(4-methoxyphenyl)cyclohexan-1-ol;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1C(C(C)CN(C)C)(O)CCCC1 YBEZEXWSGXVVIJ-UHFFFAOYSA-N 0.000 claims description 2
CXRSCELPBXNLGV-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-(1-hydroxypropan-2-yl)cyclohexan-1-ol Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C(C)CO)(O)CCCC1 CXRSCELPBXNLGV-UHFFFAOYSA-N 0.000 claims description 2
BEBTXYAQBNBPJY-UHFFFAOYSA-N 2-(4-methoxyphenyl)cyclohexan-1-one Chemical compound C1=CC(OC)=CC=C1C1C(=O)CCCC1 BEBTXYAQBNBPJY-UHFFFAOYSA-N 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
150000003461 sulfonyl halides Chemical class 0.000 claims description 2
239000000376 reactant Substances 0.000 claims 6
239000004215 Carbon black (E152) Substances 0.000 claims 3
230000002152 alkylating effect Effects 0.000 claims 3
229930195733 hydrocarbon Natural products 0.000 claims 3
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims 2
WJJGHXWZYXAOLR-UHFFFAOYSA-N 4-methyl-6-phenyl-1-oxa-3-azaspiro[4.5]decan-2-one Chemical compound CC1NC(=O)OC11C(C=2C=CC=CC=2)CCCC1 WJJGHXWZYXAOLR-UHFFFAOYSA-N 0.000 claims 2
OONFBNJEZTVGCX-UHFFFAOYSA-N [1-(1-morpholin-4-ylpropan-2-yl)-2-phenylcyclohexyl] acetate;hydrochloride Chemical compound Cl.C1CCCC(C=2C=CC=CC=2)C1(OC(C)=O)C(C)CN1CCOCC1 OONFBNJEZTVGCX-UHFFFAOYSA-N 0.000 claims 2
GTPMRVSLRYLHMQ-UHFFFAOYSA-N [2-phenyl-1-[1-(4-phenylpiperazin-1-yl)propan-2-yl]cyclohexyl] acetate;hydrochloride Chemical compound Cl.C1CCCC(C=2C=CC=CC=2)C1(OC(C)=O)C(C)CN(CC1)CCN1C1=CC=CC=C1 GTPMRVSLRYLHMQ-UHFFFAOYSA-N 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
230000020477 pH reduction Effects 0.000 claims 2
KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
RLEOZIQMUJSUMI-UHFFFAOYSA-N 1-(1-morpholin-4-ylpropan-2-yl)-2-phenylcyclohexan-1-ol;hydrochloride Chemical compound Cl.C1CCCC(C=2C=CC=CC=2)C1(O)C(C)CN1CCOCC1 RLEOZIQMUJSUMI-UHFFFAOYSA-N 0.000 claims 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 1
VGIRWKXCAKWIFE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-[1-(dimethylamino)propan-2-yl]cyclohexan-1-ol Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C(C)CN(C)C)(O)CCCC1 VGIRWKXCAKWIFE-UHFFFAOYSA-N 0.000 claims 1
NTCZPFPZYWFKBW-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)-1-hydroxycyclohexyl]propanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C(C)C(O)=O)(O)CCCC1 NTCZPFPZYWFKBW-UHFFFAOYSA-N 0.000 claims 1
CWZVAMSYBCLBAV-UHFFFAOYSA-N 2-phenyl-1-[1-(4-phenylpiperazin-1-yl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CCCC(C=2C=CC=CC=2)C1(O)C(C)CN(CC1)CCN1C1=CC=CC=C1 CWZVAMSYBCLBAV-UHFFFAOYSA-N 0.000 claims 1
HBHYQEZZQZNDNB-UHFFFAOYSA-N [1-[1-(dimethylamino)propan-2-yl]-2-(4-methoxyphenyl)cyclohexyl] acetate Chemical compound C1=CC(OC)=CC=C1C1C(C(C)CN(C)C)(OC(C)=O)CCCC1 HBHYQEZZQZNDNB-UHFFFAOYSA-N 0.000 claims 1
JANIHFWEEYYVGT-UHFFFAOYSA-N [1-[1-(dimethylamino)propan-2-yl]-2-(4-methoxyphenyl)cyclohexyl] acetate;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1C(C(C)CN(C)C)(OC(C)=O)CCCC1 JANIHFWEEYYVGT-UHFFFAOYSA-N 0.000 claims 1
MJDIWCQJUPYRAF-UHFFFAOYSA-N [1-[1-(dimethylamino)propan-2-yl]-2-phenylcyclohexyl] acetate;hydrochloride Chemical compound Cl.CN(C)CC(C)C1(OC(C)=O)CCCCC1C1=CC=CC=C1 MJDIWCQJUPYRAF-UHFFFAOYSA-N 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims 1
229940035676 analgesics Drugs 0.000 abstract description 6
239000000730 antalgic agent Substances 0.000 abstract description 6
230000003288 anthiarrhythmic effect Effects 0.000 abstract description 4
239000003589 local anesthetic agent Substances 0.000 abstract description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 2
239000003416 antiarrhythmic agent Substances 0.000 abstract 1
125000002837 carbocyclic group Chemical group 0.000 abstract 1
229960005015 local anesthetics Drugs 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 97
239000000243 solution Substances 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
239000000203 mixture Substances 0.000 description 51
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
239000000047 product Substances 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
229960001701 chloroform Drugs 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000012043 crude product Substances 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
230000000202 analgesic effect Effects 0.000 description 11
239000002585 base Substances 0.000 description 11
239000010410 layer Substances 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
239000007787 solid Substances 0.000 description 10
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
238000010992 reflux Methods 0.000 description 9
CFNVAZRMOYPPIG-UHFFFAOYSA-N C1CCCC(C=2C=CC=CC=2)C1(O)C(C)CCC1=CC=C(S(O)(=O)=O)C=C1 Chemical compound C1CCCC(C=2C=CC=CC=2)C1(O)C(C)CCC1=CC=C(S(O)(=O)=O)C=C1 CFNVAZRMOYPPIG-UHFFFAOYSA-N 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
239000000284 extract Substances 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
206010003119 arrhythmia Diseases 0.000 description 7
150000002009 diols Chemical class 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000007789 gas Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000012360 testing method Methods 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000006793 arrhythmia Effects 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 5
229910010084 LiAlH4 Inorganic materials 0.000 description 5
LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 5
244000166550 Strophanthus gratus Species 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
150000003840 hydrochlorides Chemical class 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 5
229960003343 ouabain Drugs 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229910052681 coesite Inorganic materials 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229910052906 cristobalite Inorganic materials 0.000 description 4
230000000694 effects Effects 0.000 description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
229910003002 lithium salt Inorganic materials 0.000 description 4
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210000003497 sciatic nerve Anatomy 0.000 description 1
238000012216 screening Methods 0.000 description 1
LCHWKMAWSZDQRD-UHFFFAOYSA-N silylformonitrile Chemical compound [SiH3]C#N LCHWKMAWSZDQRD-UHFFFAOYSA-N 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
229940072358 xylocaine Drugs 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA221,132A 1974-03-04 1975-03-03 1-(amino-alkyl)-2-aryl-cyclohexane alcohols and esters Expired CA1047035A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US44780474A	1974-03-04	1974-03-04

Publications (1)

Publication Number	Publication Date
CA1047035A true CA1047035A (en)	1979-01-23

Family

ID=23777825

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA221,132A Expired CA1047035A (en)	1974-03-04	1975-03-03	1-(amino-alkyl)-2-aryl-cyclohexane alcohols and esters

Country Status (3)

Country	Link
AT (1)	AT337673B (de)
CA (1)	CA1047035A (de)
DE (1)	DE2509053A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108484359A (zh) *	2018-03-20	2018-09-04	江阴技源药业有限公司	基于HMB-Ca乙醇残液回收乙醇及有效成分的方法

1975
- 1975-03-01 DE DE19752509053 patent/DE2509053A1/de not_active Withdrawn
- 1975-03-03 CA CA221,132A patent/CA1047035A/en not_active Expired
- 1975-03-04 AT AT167675A patent/AT337673B/de not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108484359A (zh) *	2018-03-20	2018-09-04	江阴技源药业有限公司	基于HMB-Ca乙醇残液回收乙醇及有效成分的方法

Also Published As

Publication number	Publication date
DE2509053A1 (de)	1975-09-11
AT337673B (de)	1977-07-11
ATA167675A (de)	1976-11-15

Publication	Publication Date	Title
US3974157A (en)	1976-08-10	1-(Amino-alkyl)-2-aryl-cyclohexane alcohols and esters
JP2664503B2 (ja)	1997-10-15	新規アミン、その使用及び製法
CA1175444A (en)	1984-10-02	Secondary amines
Poos et al.	1963	2-Amino-5-aryl-2-oxazolines. Potent new anorectic agents
AU626949B2 (en)	1992-08-13	2-amino-4 or 5-methoxycyclohexyl amides useful as analgesics
US4217305A (en)	1980-08-12	Phenylethanolamine derivatives
CA1101859A (en)	1981-05-26	1-aryloxy-2-hydroxy-3-alkylensaminopropanes and processes for their production
US5225585A (en)	1993-07-06	Production of fluoxetine and new intermediates
CA1338934C (en)	1997-02-25	3-aminomethyl derivatives of indane, indoline and ¬dihydro-benzo\|-furane and thiophene
BG61056B2 (bg)	1996-09-30	Заместени пропаноламинови и морфолинови производни
EP0773937A1 (de)	1997-05-21	Von arylpiperazinen abgeleitete piperzide und ihre verwendung als medikament
CA1092158A (en)	1980-12-23	Cinnamyl-alkyl-1-naphthylamines
JPS6215546B2 (de)	1987-04-08
NZ204901A (en)	1987-03-06	N-(2-phenyl-2-hydrocarbyloxyethyl)-n-(omega-phenylalkyl)amines
FR2958291A1 (fr)	2011-10-07	Procede de preparation de derives d'amino-benzofurane
EP0886636A1 (de)	1998-12-30	Neue 1-/(piperazin-1-yl-)aryl(oxy/amino)carbonyl/-4-aryl-piperidin derivate als selektive 5-ht-1d.beta.-rezeptor antagonisten
EP0084920B1 (de)	1989-04-19	Verbindungen verwendbar als Zwischenprodukte oder Ausgangsstoffe zur Herstellung von therapeutisch verwendbaren Phenyl-azacycloalkanen
WO1997014689A1 (fr)	1997-04-24	Derives d'amines cycliques d'aryl-piperazines, leur preparation et les compositions pharmaceutiques les contenant
CA1108633A (en)	1981-09-08	1-aryloxy-2-hydroxy-3-aminopropanes and process for preparing same
US4720586A (en)	1988-01-19	Substituted 3,4-dihydroxy-phenylethylamino compounds
US4927968A (en)	1990-05-22	Chemical intermediates and process
US4620015A (en)	1986-10-28	Synthesis of β-((2-methylpropoxy)methyl)-N-phenyl-N-(phenylmethyl)-1-pyrrolidineethanamine
COSGROVE et al.	1956	Tetrazole derivatives I. Tetrazole alkamine ethers
AU609067B2 (en)	1991-04-26	Compounds useful as intermediates for the production of substituted 1-pyridyloxy-3-indolyalkylamino-2- propanols
KR840000103B1 (ko)	1984-02-11	1, 1'-비페닐-2-일 알킬아민 유도체의 제조방법

CA1047035A - 1-(amino-alkyl)-2-aryl-cyclohexane alcohols and esters - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=23777825

Family Applications (1)

Country Status (3)

Cited By (1)

Cited By (1)

Also Published As

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