Advertisement

Chemistry of Natural Compounds

, Volume 16, Issue 4, pp 397–402 | Cite as

Synthesis and study of the structure of new N-substituted 2-methyl-5-(1-methylethyl) cyclohexylamines

  • I. I. Bardyshev
  • N. G. Kozlov
  • T. K. Vyalimyaé
  • T. I. Pekhk
Article
  • 34 Downloads

Abstract

Original methods of synthesizing N-substituted 2-methyl-5-(1-methylethyl)cyclohexylamines by hydroamination reactions of (+)-S-carvone with aliphatic nitriles and the hydroamination of some aldehydes and ketones with (+)-S-carvone oxime have been developed. The optimum conditions for performing these processes has been selected. It has been established by13C NMR that the reactions studied form a mixture of N-substituted carvo-, isocarvo-, neocarvo-, and neoisocarvomenthylamines in a ratio of 65:20:10:5. As a result of the investigation, 11 secondary amines of the p-menthane series not previously described in the literature have been isolated and characterized. The absolute configurations of the compounds synthesized have been determined.

Keywords

Oxime Space Velocity Secondary Amine Carvone Cyclohexylamine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    H. Haruta, H. Yagi, and T. Iwata, Agr. Biol. Chem.,38, No. 1, 141 (1974).CrossRefGoogle Scholar
  2. 2.
    Japanese Patent No. 48-43612 (1973); Chem. Abstr.,81, 115912 (1974).Google Scholar
  3. 3.
    J. Blanc, P. Carnero, and B. Gastambide, Bull. Soc. Chim. Fr., No. 8, 1864 (1964).Google Scholar
  4. 4.
    H. Feltkamp, F. Koch, and T. N. Thanh, Ann. Chem.,707, 78 (1967).CrossRefGoogle Scholar
  5. 5.
    I. I. Bardyshev and N. G. Kozlov, Favorable Decision on USSR Patent Application No. 2,732,661 (1979).Google Scholar
  6. 6.
    N. S. Kozlov, S. I. Kozintsev, and L. V. Naumova, Dokl. Akad. Nauk SSSR,226, No. 6, 1341 (1976).Google Scholar
  7. 7.
    N. S. Kozlov, L. I. Moiseenok, and S. I. Kozintsev, Dokl. Akad. Nauk SSSR,241, No. 6, 1345 (1978).Google Scholar
  8. 8.
    I. I. Bardyshev, N. G. Kozlov, and A. A. Geller, Izv. Akad. Nauk BSSR, Ser. Khim., Nauk., No. 3, 116 (1979).Google Scholar
  9. 9.
    N. S. Kozlov, A. A. Tarasevich, S. I. Kozintsev, and L. V. Gladkikh, Dokl. Akad. Nauk SSSR,244, No. 5, 1130 (1979).Google Scholar
  10. 10.
    N. S. Kozlov, V. A. Tarasevich, S. I. Kozintsev, and L. V. Gladkikh, Dokl. Akad. Nauk BSSR,23, No. 10, 910 (1979).Google Scholar
  11. 11.
    R. Rygade and E. Sylow, Acta Chem. Scand.,17, 2025 (1963).CrossRefGoogle Scholar
  12. 12.
    T. I. Pekhk, É. T. Kippmaa, V. I. Lysenkova, and I. I. Bardyshev, Zh. Org. Khim.,15, 1877 (1979).Google Scholar
  13. 13.
    J. Cassan, Bull. Soc. Chim. Fr., Bo. 10, 3624 (1969).Google Scholar

Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • I. I. Bardyshev
  • N. G. Kozlov
  • T. K. Vyalimyaé
  • T. I. Pekhk

There are no affiliations available

Personalised recommendations