Detail of "5382-18-3"

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Synthesis of 1-tert-Butyl-4-chloropiperidine: Generation of an N-tert-Butyl Group by the Reaction of Dimethyliminium Salt with Methylmagnesium Chloride

Synthesis of 1-tert-Butyl-4-chloropiperidine: Generation of an N-tert-Butyl Group by the Reaction of Dimethyliminium Salt with Methylmagnesium Chloride. Amato, Joseph S. 5382-18-3 which is the cas registry number is also used here.; Chung, John Y. L.; Cvetovich, Raymond J.; Gong, Xiaoyi; McLaughlin, Mark; Reamer, Robert A. (Departments of Process Research and Analytical Research, Merck Research Laboratories, Rahway, NJ 07065, USA). Journal of Organic Chemistry, 70(5), 1930-1933 (English) 2005 American Chemical Society. CODEN: JOCEAH. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Two efficient routes to 1-tert-butyl-4-chloropiperidine are described. In the first route, the key thionyl chloride mediated chlorination reaction features the use of tetrabutylammonium chloride as an additive that effectively suppresses the formation of an elimination-derived side product. In the second route, a novel alternative synthesis of 1-tert-butyl-4-chloropiperidine was developed in which the tertiary-Bu group on the nitrogen is efficiently generated through the addn. of methylmagnesium chloride to a dimethyliminium salt in 71% overall yield. .