GB725875A - Process for the manufacture of n-methyl-ª‰-cyclohexen-(1)-yl-ethylamine and intermediates for the preparation thereof - Google Patents

Process for the manufacture of n-methyl-ª‰-cyclohexen-(1)-yl-ethylamine and intermediates for the preparation thereof

Info

Publication number
GB725875A
GB725875A GB14323/53A GB1432353A GB725875A GB 725875 A GB725875 A GB 725875A GB 14323/53 A GB14323/53 A GB 14323/53A GB 1432353 A GB1432353 A GB 1432353A GB 725875 A GB725875 A GB 725875A
Authority
GB
United Kingdom
Prior art keywords
cyclohexen
ethylamine
methyl
manufacture
aryl
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
GB14323/53A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB725875A publication Critical patent/GB725875A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/86—Separation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
    • C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

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

Abstract

The invention comprises compounds of the general formula <FORM:0725875/IV (b)/1> wherein R is an aryl or lower alkyl radical. It also comprises a process for the manufacture of N-methyl-b -cyclohexen-(1)-yl-ethylamine by reacting b -cyclohexen-(1)-yl-ethylamine in the presence of a condensing agent with a ketone of the general formula C6H5COR where R is an aryl or lower alkyl radical, to form the corresponding Schiff base, reacting the latter with a methylating agent and treating the condensation product formed with an alkaline agent so as to produce N-methyl-b -cyclohexen-(1)-yl-ethylamine. In an example, b -cyclohexen-(1)-yl-ethylamine and benzophenone are refluxed in xylene with the complex salt of b -cyclohexen-(1) - yl - ethylamine with zinc chloride. The product obtained, after separation of the zinc chloride is methylated by reaction with dimethyl sulphate and the methylation product is decomposed with sodium hydroxide to give N - methyl - b - cyclohexen - (1) - yl - ethylamine. Specification 685,747 is referred to.
GB14323/53A 1952-05-29 1953-05-21 Process for the manufacture of n-methyl-ª‰-cyclohexen-(1)-yl-ethylamine and intermediates for the preparation thereof Expired GB725875A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE725875X 1952-05-29

Publications (1)

Publication Number Publication Date
GB725875A true GB725875A (en) 1955-03-09

Family

ID=6635071

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14323/53A Expired GB725875A (en) 1952-05-29 1953-05-21 Process for the manufacture of n-methyl-ª‰-cyclohexen-(1)-yl-ethylamine and intermediates for the preparation thereof

Country Status (1)

Country Link
GB (1) GB725875A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4020104A (en) * 1976-09-20 1977-04-26 The Upjohn Company Process for isomerizing cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4020104A (en) * 1976-09-20 1977-04-26 The Upjohn Company Process for isomerizing cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer

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