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Paper | Regular issue | Vol 68, No. 6, 2006, pp.1173-1183
Published online, 11th April, 2006
DOI: 10.3987/COM-06-10717
Concise Synthesis of 3-Arylpiperidines

Meng-Yang Chang,* Ru-Ting Hsu, Hua-Ping Chen, and Pei-Jung Lin

*Department of Applied Chemistry, National University of Kaohsiung, Kaohsiung 811, Taiwan, R.O.C.

Abstract

We present an easy and straightforward synthesis of 3-arylpiperidines by Grignard addition of piperidin-3-one with different arylmagnesium bromide reagents and acidic dehydroxylation of the resulting tertiary alcohol with the combination of triethylsilane and boron trifluoride etherate. This facile strategy was further used to synthesize preclamol. A highly regioselective dehydration of 3-arylpiperidin-3-ol with boron trifluoride etherate was investigated for preparing 3-aryl-1,4,5,6-tetrahydropyridine skeleton. A novel selenium dioxide mediated dihydroperoxidation of 3-aryl-1,4,5,6-tetrahydropyridine was also examined.