1-Benzyl-4-chloromethylpiperidine: A Building Block in the Synthesis of Compounds of Pharmacological Interest

María Isabel Rodríguez-Franco; María Isabel Fernández-Bachiller

doi:10.1055/s-2002-28517

PAPER

1-Benzyl-4-chloromethylpiperidine: A Building Block in the Synthesis of Compounds of Pharmacological Interest

María Isabel Rodríguez-Franco*, María Isabel Fernández-Bachiller
Instituto de Química Médica (C.S.I.C.), Juan de la Cierva 3, 28006 Madrid, Spain
Fax: +34(91)5644853; e-Mail: IsabelRguez@iqm.csic.es;

Abstract

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Abstract

The first synthesis of 1-benzyl-4-(chloromethyl)piperidine (1) is described, together with its application in the synthesis of potential pharmaceuticals. Reaction of 1 with several purines in basic medium proceed through the initial formation of 1-benzyl-1-azoniabicyclo[2.2.1]heptane system, which then undergoes nucleophilic attack at two different carbons, yielding N-benzylpiperidine and N-benzylpyrrolidine derivatives.

Key words

N-benzylpiperidines - N-benzylpyrrolidines - purines - alkylations - rearrangements

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References

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