Development of a Scaleable Route for the Production ofcis-N-Benzyl-3-methylamino-4-methylpiperidine

David H. Brown Ripin,Stefan Abele,Weiling Cai,Todd Andrew Blumenkopf,Jeffrey M. Casavant,Jonathan L. Doty,Mark E Flanagan,Christian Koecher,Klaus Wilhelm Laue,Keith E Mccarthy,Cliff Meltz, Mike Munchhoff,Kees Pouwer, Bharat Shah,Jianmin Sun,J John Teixeira,Ton R Vries,David A. Whipple,Glenn Wilcox

ORGANIC PROCESS RESEARCH & DEVELOPMENT（2003）

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Abstract

The synthesis of cis-N-benzyl-3-methylamino-4-methylpiperidine (5) via hydroboration of tetrahydropyridine 3 followed by oxidation and reductive amination was optimized and scaled up to produce 10-kg quantities of product. Three routes to 3 were identified, and the reduction of pyridinium salt 7 was selected as the most preferable to run on-scale. The hydroboration and oxidative workup were carefully studied to optimize throughput on that transformation, as was the reductive amination.

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Key words

<i>cis</i>-<i>n</i>-benzyl-3-methylamino-4-methylpiperidine,scaleable route,production

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