H. Fakhraian, M. B. P. Riseh
Jun 1, 2008
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Influential Citations
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Journal
Organic Preparations and Procedures International
Abstract
1 -(2-Phenethyl)-4-piperidone (4) is a key intermediate for the preparation of fenranyl (analgesi~),I-~ its analogues6 and other medicaments.',* The most widely-used method for the synthesis of 4-piperidones is the Dieckmann cyclization of aminodicarboxylate esters which is a multi-steps procedure that occurs under equilibrium condition and is influenced by multiple parameters? The general method of McElvain for the preparation of 4-pipendones consisting in the condensation of appropriate primary amine with two equivalents of methyl (or ethyl) acrylate, the cyclization of the resulting bis-ester (Dieckmann reaction) followed by hydrolysis and decarboxylation of the resulting cyclic product, is a well-known method (Scheme ]).lo