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An efficient synthesis of 3-arylpiperidines

✍ Scribed by H. J. J. Loozen; F. T. L. Brands

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 437 KB
Volume: 100
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19811000909

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✦ Synopsis

Abstract

An alternative route to 3‐arylpiperidines is described, thereby circumventing traditional Michael addition of substituted phenylacetonitriles to methyl acrylate. Treatment of (3‐methoxyphenyl)acetonitrile (2) with the THP ether of 3‐bromo‐1‐propanol, followed by chromic acid oxidation and saponification provided 2‐(3‐methoxyphenyl)glutaric acid (6). Treatment of the corresponding anhydride 7 with alkyl‐ and arylalkylamines provided the imides 8a‐c. Replacement of the methoxy group by a benzyloxy group, followed by LiAlH~4~ reduction and a catalytic reduction provided 1, 12 and 13.

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