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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 10, pp 1107–1113 | Cite as

Esters of heterocyclic γ-amino alcohols

VI. Synthesis of substituted cis-3-aminomethyl-4-hydroxypiperidines and their acyl derivatives
  • E. T. Golovin
  • A. P. Nikiforova
  • B. V. Unkovskii
Article
  • 26 Downloads

Abstract

Reduction of cis-3-cyano-4-hydroxypiperidines with lithium aluminum hydride (LAH) gave cis-3-aminomethyl-4-hydroxypiperidines, which were converted to cis-3-dimethylaminomethyl-4-hydroxypiperidines by methylation with formaldehyde and formic acid. Acylation of the methylated compounds with benzoyl and cinnatnoyl chlorides gave the corresponding esters. Condensation of cis-3-aminomethyl-4-hydroxypiperidines with formaldehyde gave perhydropyrido[3,4-e][1,3]oxazines, which were converted to 3-methylaminomethyl-4-hydroxypiperidines by means of LAH. The cis isomers of the corresponding O,N-diacyl derivatives of these amino alcohols were obtained by acylation with acetic anhydride and benzoyl and cinnamoyl chlorides.

Keywords

Alcohol Methylated Chloride Ester Formaldehyde 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • E. T. Golovin
    • 1
  • A. P. Nikiforova
    • 1
  • B. V. Unkovskii
    • 1
  1. 1.M. V. Lomonosov Moscow Institute of Fine Chemical TechnologyMoscow

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