GB708771A - Improvements in or relating to aryl aliphatic amines and their salts - Google Patents

Improvements in or relating to aryl aliphatic amines and their salts

Info

Publication number
GB708771A
GB708771A GB6350/52A GB635052A GB708771A GB 708771 A GB708771 A GB 708771A GB 6350/52 A GB6350/52 A GB 6350/52A GB 635052 A GB635052 A GB 635052A GB 708771 A GB708771 A GB 708771A
Authority
GB
United Kingdom
Prior art keywords
acid
diphenyl
solution
carbon atoms
resultant
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
GB6350/52A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB708771A publication Critical patent/GB708771A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • 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
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton

Landscapes

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

Abstract

The invention comprises new arylaliphatic amines of formula <FORM:0708771/IV (b)/1> in which R1 and R2 represent alkyl radicals, normal or branched, containing from 1 to 4 carbon atoms and n is 4, 5 or 6, and their acid addition salts. The new compounds are obtained by condensing benzophenone with a phenoxyalkyl magnesium halide in which the alkyl chain contains from 4 to 6 carbon atoms, dehydrating the resultant diphenyl phenoxyalkyl carbinol with a concentrated mineral acid, hydrogenating the alkene thus obtained, treating the resultant alkane with a concentrated halogen acid and reacting the halogenoalkane thus formed with a dialkylamine in which the alkyl groups contain from 1 to 4 carbon atoms with or without subsequent conversion of the resultant tertiary amine into an acid addition salt by treatment with an acid. In the examples a solution of sodium phenate in alcohol is heated with 1 : 4 dibromobutane and the phenoxybrombutane formed is separated; it is dissolved in ether and is converted to phenoxy butyl magnesium bromide by the addition of magnesium; benzophenone is added in ethereal solution and the complex is decomposed by ice and sulphuric acid; a crystallic residue, consisting of diphenyl phenoxybutyl carbinol is obtained from the ethereal solution and is dehydrated by heating with fuming hydrochloric acid; diphenylphenoxypentene is separated and is hydrogenated in alcoholic solution in the presence of Raney nickel and diphenylphenoxypentane is crystallized from the resulting solution; the diphenylphenoxypentane is dissolved in glacial acetic acid and treated with hydrobromic acid to give diphenylbromopentane which is heated with diethylamine; 1 : 1 diphenyl-5 diethylamino-pentane is obtained and it can be converted to its hydrochloride by treatment with hydrochloric acid. In the same way 1 : 1-diphenyl-6-diethyl-aminohexane is obtained from bromophenoxypentane prepared from 1 : 5-dibromopentane and 1 : 1-diphenyl-7-diethylaminoheptane is prepared from 1 : 6-dibromohexane.
GB6350/52A 1951-03-15 1952-03-11 Improvements in or relating to aryl aliphatic amines and their salts Expired GB708771A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR708771X 1951-03-15

Publications (1)

Publication Number Publication Date
GB708771A true GB708771A (en) 1954-05-12

Family

ID=9069128

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6350/52A Expired GB708771A (en) 1951-03-15 1952-03-11 Improvements in or relating to aryl aliphatic amines and their salts

Country Status (1)

Country Link
GB (1) GB708771A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3510560A (en) * 1964-09-30 1970-05-05 Smithkline Corp Method of producing anti-adrenal activity with diarylalkylamines
US4034011A (en) * 1974-12-24 1977-07-05 Eli Lilly And Company 1,1-Diphenyl-4-(substituted-amino)butanes
US4098890A (en) 1974-12-24 1978-07-04 Eli Lilly And Company Method for treating arrhythmia

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3510560A (en) * 1964-09-30 1970-05-05 Smithkline Corp Method of producing anti-adrenal activity with diarylalkylamines
US4034011A (en) * 1974-12-24 1977-07-05 Eli Lilly And Company 1,1-Diphenyl-4-(substituted-amino)butanes
US4098890A (en) 1974-12-24 1978-07-04 Eli Lilly And Company Method for treating arrhythmia

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