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Chemistry of Heterocyclic Compounds

, Volume 28, Issue 12, pp 1389–1394 | Cite as

Stereochemistry of the reactions of cyanohydrins of substituted 4-piperidones with ammonia and amines. Synthesis and structure of substituted 4-amino-, 4-methylamino-, and 4-dimethylamino-4-cyanopiperidines

  • B. V. Unkovskii
  • M. Yu. D'yakov
  • T. D. Sokolova
  • V. B. Rozhnov
  • G. V. Cherkaev
Article
  • 46 Downloads

Abstract

The action of ammonia, methylamine, or dimethylamine on substituted 4-hydroxy-4-cyanopiperidines in a modified Strecker synthesis gave mixtures of stereoisomers of the corresponding 4-amino-, 4-methylamino- and 4-dimethylamino-4-cyanopiperidine. 1H and 13C NMR spectroscopy was used to determine the structure of these products. Unusual stereocontrol was found for the reaction of methylamine and dimethylamine with cyanohydroxypiperidine with substituents at C(2) and C(5) in the ring.

Keywords

Spectroscopy Ammonia Organic Chemistry Methylamine Dimethylamine 
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 1993

Authors and Affiliations

  • B. V. Unkovskii
    • 1
    • 2
  • M. Yu. D'yakov
    • 1
    • 2
  • T. D. Sokolova
    • 1
    • 2
  • V. B. Rozhnov
    • 1
    • 2
  • G. V. Cherkaev
    • 1
    • 2
  1. 1.M. V. Lomonosov Moscow State Institute of Fine Chemical TechnologyMoscow
  2. 2.Institute of Chemical Sciences of the Kazakh Academy of SciencesAlma-Ata

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