Development of a scaleable route for the production of cis-N-benzyl-3-methylamino-4-methylpiperidine

…, C Meltz, M Munchhoff, K Pouwer, B Shah…

Index: Brown Ripin, David H.; Abele, Stefan; Cai, Weiling; Blumenkopf, Todd; Casavant, Jeffrey M.; Doty, Jonathan L.; Flanagan, Mark; Koecher, Christian; Laue, Klaus W.; McCarthy, Keith; Meltz, Cliff; Munchhoff, Mike; Pouwer, Kees; Shah, Bharat; Sun, Jianmin; Teixeira, John; Vries, Ton; Whipple, David A.; Wilcox, Glenn Organic Process Research and Development, 2003 , vol. 7, # 1 p. 115 - 120

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Citation Number: 29

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 ...