GB722301A - Bis[ª‰-(ortho-hydrocarbonoxyphenyl)isopropyl]amines - Google Patents

Bis[ª‰-(ortho-hydrocarbonoxyphenyl)isopropyl]amines

Info

Publication number
GB722301A
GB722301A GB26789/52A GB2678952A GB722301A GB 722301 A GB722301 A GB 722301A GB 26789/52 A GB26789/52 A GB 26789/52A GB 2678952 A GB2678952 A GB 2678952A GB 722301 A GB722301 A GB 722301A
Authority
GB
United Kingdom
Prior art keywords
hydrocarbonoxyphenyl
ortho
isopropyl
butyl
alcohol
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
GB26789/52A
Inventor
Richard Voorhees Heinzelmann
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
Priority to GB26789/52A priority Critical patent/GB722301A/en
Publication of GB722301A publication Critical patent/GB722301A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups

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 bis[b -(ortho-hydrocarbonoxyphenyl)isopropyl]-amines <FORM:0722301/IV (b)/1> wherein R is a hydrocarbon radical having from one to seven carbon atoms inclusive, and salts thereof, and their preparation by reducing, with hydrogen under pressure and a hydrogenation catalyst, e.g. Raney nickel, platinum oxide, palladium or copper chromite, a solution of an ortho-hydrocarbonoxyphenyl acetone and ammonia or an ortho-hydrocarbonoxyphenyl-isopropylamine. The reaction may be effected in a solvent such as an ester, alcohol or hydrocarbon. Mixtures of diastereoisomeric amines thus obtained may be separated by the fractional crystallization of their salts or by forming a complex with an alcohol, e.g. methanol, ethanol, propanol, ethylene glycol, propylene glycol, cyclohexanol and diethylene glycol monoethyl ether, and separating the so-formed complexes by their different solubilities in excess of alcohol. Examples disclose the production of compounds in which R represents methyl, benzyl, isopropyl, n-propyl and in addition n-hexyl. Compounds are also mentioned in which R represents ethyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-amyl, isoamyl, sec-amyl, 2-methylbutyl, 1-methylpentyl, 2-methylpentyl, cyclopentyl, cyclohexyl and phenyl. o-Hydrocarbonoxyphenylacetones are obtained by reacting o-hydrocarbonoxybenzaldehydes and nitroethane in the presence of a basic condensation catalyst. o-Hydrocarbonoxybenzaldehydes are obtained by condensing in the presence of sodium ethoxide, salicylaldehyde with a hydrocarbon halide, e.g. benzyl chloride, isopropyl iodide, n-propyl iodide and n-hexyl bromide.
GB26789/52A 1952-10-24 1952-10-24 Bis[ª‰-(ortho-hydrocarbonoxyphenyl)isopropyl]amines Expired GB722301A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB26789/52A GB722301A (en) 1952-10-24 1952-10-24 Bis[ª‰-(ortho-hydrocarbonoxyphenyl)isopropyl]amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB26789/52A GB722301A (en) 1952-10-24 1952-10-24 Bis[ª‰-(ortho-hydrocarbonoxyphenyl)isopropyl]amines

Publications (1)

Publication Number Publication Date
GB722301A true GB722301A (en) 1955-01-19

Family

ID=10249227

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26789/52A Expired GB722301A (en) 1952-10-24 1952-10-24 Bis[ª‰-(ortho-hydrocarbonoxyphenyl)isopropyl]amines

Country Status (1)

Country Link
GB (1) GB722301A (en)

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