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Condensation of 1,2,5-trimethyl-4-piperidone with p-diethynlbenzene

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A mixture of stereoisomeric diacetylenic piperidols was obtained by the reaction of 1,2,5-trimethyl-4-piperidone with p-diethynylbenzene in liquid ammonia in the presence of sodium amide. Each of the two pure alcohol and glycol geometrical isomers were isolated by chromatography with columns filled with aluminum oxide. Assumptions relative to the three-dimensional structure of the synthesized compounds are expressed on the basis of the principles of conformational analysis, the chromatographic data, and a study of the IR and NMR spectra. Saturated piperidols were obtained by catalytic hydrogenation on a Raney nickel catalyst.

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Authors and Affiliations

  1. Institute of Chemical Sciences, Academy of Sciences of the Kazakh SSSR, Alma-Ata

    I. N. Azerbaev, Yu. G. Bosyakov & K. B. Erzhanov

Authors
  1. I. N. Azerbaev
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  2. Yu. G. Bosyakov
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  3. K. B. Erzhanov
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1646–1651, December, 1970.

The authors thank O. V. Agasikin for this assistance in interpreting the IR and NMR spectra.

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Azerbaev, I.N., Bosyakov, Y.G. & Erzhanov, K.B. Condensation of 1,2,5-trimethyl-4-piperidone with p-diethynlbenzene. Chem Heterocycl Compd 6, 1536–1541 (1970). https://doi.org/10.1007/BF00522576

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  • DOI: https://doi.org/10.1007/BF00522576

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