Abstract

1. A method was developed for the reductive dequaternization of the quaternary ammonium salts ofγ-piperidinols using lithium in liquid ammonia, with a retention of the piperidine ring and the functional groups. 2. For the N-methyl-N-alkylpiperidinium salts the main direction of the dequaternization reaction is demethylation without opening the piperidine ring. 3. For C2-gem-substituted piperidines the main direction of the reaction is opening of the ring, with the formation of the noncyclic tertiary amine. 4. The configuration of the alkyl substituents on the carbon atom of the ring, or on the nitrogen atom, is without effect on the dequaternization reaction. 5. A method was proposed for the synthesis of N-alkylpiperidinols, starting with the N-methyl analogs, which method can be used with success to correlate the structure of piperidine derivatives.

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