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

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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.

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Authors
  1. I. I. Bardyshev
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  2. N. G. Kozlov
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  3. T. K. Vyalimyaé
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  4. T. I. Pekhk
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Additional information

Institute of Physical Organic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk. Institute of Cybernetics, Academy of Sciences of the Estonian SSR, Tallin. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 546–553, July–August, 1980.

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Bardyshev, I.I., Kozlov, N.G., Vyalimyaé, T.K. et al. Synthesis and study of the structure of new N-substituted 2-methyl-5-(1-methylethyl) cyclohexylamines. Chem Nat Compd 16, 397–402 (1980). https://doi.org/10.1007/BF00568377

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  • DOI: https://doi.org/10.1007/BF00568377

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