Tetrahedron

Synthesis of sterically hindered 1-arylpyrrolidines and 1-arylpiperidines by condensation of primary aromatic amines with cyclic ethers or diols

RE Walkup, S Searles

Index: Walkup, Robert E.; Searles, Scott Tetrahedron, 1985 , vol. 41, # 1 p. 101 - 106

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Citation Number: 18

Abstract

A variety of 1-(o-alkylphenyl)-and 1-(o-o'-dialkylphenyl)-pyrrolidines and-piperidines were prepared by the gas phase alumina mediated condensation of tetrahydrofuran (THF), tetrahydropyran (THP) or the corresponding diols with primary aromatic amines in fair to high yield. This methodology can also be used for the synthesis of 1- phenylhexahydroazepine from aniline. A mechanistic interpretation of the catalytic action ...

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