GB1311580A - 4-substituted phenyl cyclohexylamines and the preparation thereof - Google Patents

4-substituted phenyl cyclohexylamines and the preparation thereof

Info

Publication number
GB1311580A
GB1311580A GB3451371A GB3451371A GB1311580A GB 1311580 A GB1311580 A GB 1311580A GB 3451371 A GB3451371 A GB 3451371A GB 3451371 A GB3451371 A GB 3451371A GB 1311580 A GB1311580 A GB 1311580A
Authority
GB
United Kingdom
Prior art keywords
substituted phenyl
alkyl
followed
trans
cis
Prior art date
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
GB3451371A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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.)
Filing date
Publication date
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB1311580A publication Critical patent/GB1311580A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings

Landscapes

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

Abstract

1311580 4-(Substituted phenyl)cyclohexylamines and derivatives UPJOHN CO 22 July 1971 [31 Aug 1970] 34513/71 Heading C2C Novel compounds of the general formula I wherein # denotes cis or trans configurations or mixtures thereof; R is C 1-4 alkyl, fluorine, chlorine, bromine, trifluoromethyl or C 1-4 alkoxyl; R<SP>1</SP> is hydrogen or methyl; R<SP>2</SP> is hydrogen, methyl, alkoxy carbonyl wherein the alkyl is C 1-4 , C 1-3 alkanoyl, C 1-3 alkylsulphonyl, C 6-10 arylsulphonyl, alkylcarbamoyl wherein alkyl is C 1-4 , ring monosubstituted C 6-10 aroyl- C 1-6 -alkyl where the substituent is R defined above, or bis (ring monosubstituted phenyl) C 1-6 alkyl where the substituent is R as above; or R<SP>1</SP> and R<SP>2</SP> together with the nitrogen attached thereto is unsubstituted or monosubstituted pyrrolidino, piperidino, or hexamethyleneimino and acid addition salts thereof may be prepared from an R substituted phenyl magnesium bromide and 4-hydroxycyclohexanone to form cis and trans isomers of a 4- (substituted phenyl) - 1,4-cyclohexanediol, followed by oxidation to yield the corresponding 4-(substituted phenyl)- 4-hydroxycyclohexanone, treating this with a dehydrating agent such as a strong acid to yield the 4-(substituted phenyl)-3-cyclohexen- 1-one followed by reduction at the 1-position to give 4-(substituted phenyl)-3-cyclohexen-1-ol and reduction at the 3-position to yield cis and trans 4- (substituted phenyl ) cyclohexanols which may be separated into isomers, then treatment with an alkyl (or aryl) sulphonyl halide in the presence of base to yield cis and/or trans 4-(substituted phenyl) cyclohexanol alkyl (or aryl) sulphonate, followed by reaction with sodium azide to give cis and/or trans 4-(substituted phenyl)-cyclohexan-1-yl azide which on reduction gives the compound I in which R 1 and R 2 are hydrogen, followed by known reactions to introduce the alternative R 1 an R 2 radicals. In particular reaction with an α,#-dihaloalkane, a di(haloalkyl)ether, or a di(haloalkyl) amine yields the pyrrolidino, &c. radicals, and reaction with a 2,2-dimethyl-1,3-propanediol ketal of a ring monosubstituted aroyl alkyl halide followed by hydrolysis yields compounds in which R<SP>2</SP> is ring monosubstituted aroyl alkyl. Pharmaceutical compositions of the compounds I show CNS activity (either stimulant or depressant) when administered orally or parenterally with the usual excipients.
GB3451371A 1970-08-31 1971-07-22 4-substituted phenyl cyclohexylamines and the preparation thereof Expired GB1311580A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US6857370A 1970-08-31 1970-08-31

Publications (1)

Publication Number Publication Date
GB1311580A true GB1311580A (en) 1973-03-28

Family

ID=22083413

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3451371A Expired GB1311580A (en) 1970-08-31 1971-07-22 4-substituted phenyl cyclohexylamines and the preparation thereof

Country Status (6)

Country Link
BE (1) BE772010A (en)
CH (1) CH555318A (en)
DE (1) DE2139239A1 (en)
FR (1) FR2103647B1 (en)
GB (1) GB1311580A (en)
NL (1) NL7111810A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4537698A (en) * 1982-05-28 1985-08-27 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline piperidine derivatives
GB2195999A (en) * 1986-09-10 1988-04-20 Ici Plc Tertiary amine compounds
US4975445A (en) * 1989-12-06 1990-12-04 Warner-Lambert Company Substituted cyclohexenes as central nervous system agents
WO2003037879A1 (en) * 2001-10-29 2003-05-08 Grünenthal GmbH Substituted (1h)-quinoxalin-2-one compounds and substituted 4-aryl- and 4-heteroarylcyclohexane compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960961A (en) * 1970-08-31 1976-06-01 The Upjohn Company 4'-Fluoro-4-{[4-(phenyl)cyclohexyl]amino}butyrophenones and the salts thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4537698A (en) * 1982-05-28 1985-08-27 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline piperidine derivatives
GB2195999A (en) * 1986-09-10 1988-04-20 Ici Plc Tertiary amine compounds
US4975445A (en) * 1989-12-06 1990-12-04 Warner-Lambert Company Substituted cyclohexenes as central nervous system agents
WO2003037879A1 (en) * 2001-10-29 2003-05-08 Grünenthal GmbH Substituted (1h)-quinoxalin-2-one compounds and substituted 4-aryl- and 4-heteroarylcyclohexane compounds

Also Published As

Publication number Publication date
BE772010A (en) 1972-02-29
FR2103647A1 (en) 1972-04-14
DE2139239A1 (en) 1972-03-02
FR2103647B1 (en) 1975-02-07
CH555318A (en) 1974-10-31
NL7111810A (en) 1972-03-02

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees