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

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

References

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1

This paper comprises a part of M. I. Fernández-Bachiller’s Ph.D. Thesis.