Synthesis of 1-Substituted 4-Phenyl-4-piperidinol Derivatives as Possible Analgesic.

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Author(s)

Abstract

1-Phenethyl-and 1-[2-(N-alkylanilino)ethyl]-3-alkyl-4-piperidinepropionates were synthesized for physiological evaluation as analgesics. Phenethylamine was condensed with formaldehyde and various alkylmalonic acids, followed by decarboxylation and esterification, to furnish the corresponding 2-alkyl-3-phenethylaminopropionates, which were also prepared from the same amine and 2-alkylacrylates. These were then converted to 3, 3'-(phenethylimino) dipropionic ester derivatives, which were condensed by the Dieckmann method and the crude keto esters were directly submitted to ketonic fission. 1-Phenethyl-3-alkyl-4-piperidinones thus obtained formed a viscous oil, which was allowed to react with phenyllithium and the products were treated with propionic anhydride, to give the ultimate compounds. From N-alkyl-N-Phenylethylenediamine in place of phenethylamine the corresponding piperidinol propionates were similarly prepared. The results of the pharmacological examination of these compounds were described briefly.

Journal

  • Chemical and Pharmaceutical Bulletin

    Chemical and Pharmaceutical Bulletin 10(1), 55-60, 1962

    The Pharmaceutical Society of Japan

Codes

  • NII Article ID (NAID)
    110003618718
  • NII NACSIS-CAT ID (NCID)
    AA00602100
  • Text Lang
    ENG
  • ISSN
    0009-2363
  • NDL Article ID
    9244957
  • NDL Source Classification
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-D167
  • Data Source
    NDL  NII-ELS  J-STAGE 
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