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Stereochemistry of the dequaternization of 1,1-dialkyl-4-oxopiperidinium salts

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Conclusions

  1. 1.

    1-Alkyl-14-methyl-4-oxopiperidinium salts can be dealkylated quantitatively by means of lithium in liquid ammonia with preservation of the piperidine ring and the ketone function.

  2. 2.

    The course of the dealkylation depends neither on the position of the substituents in the ring, nor on their configuration.

  3. 3.

    The breaking of the N+-C bond depends on the nature of the alkyl substituent.

  4. 4.

    A method is proposed for the synthesis of 1-alkyl-4-piperidones from 1-methyl-4-piperidones which may find application for the structural correlation of 4-piperidones.

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Literature cited

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    G. T. Katvalyan and É. L. Mistryukov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11 (1968).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2023–2027, September, 1969.

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Katvalyan, G.T., Mistryukov, É.A. Stereochemistry of the dequaternization of 1,1-dialkyl-4-oxopiperidinium salts. Russ Chem Bull 18, 1868–1872 (1969). https://doi.org/10.1007/BF00905826

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Keywords

  • Ammonia
  • Lithium
  • Ketone
  • Piperidine
  • Structural Correlation