26822-30-0Relevant academic research and scientific papers
Synthesis of 1-tert-butyl-4-chloropiperidine: Generation of an N-tert-butyl group by the reaction of a dimethyliminium salt with methylmagnesium chloride
Amato, Joseph S.,Chung, John Y. L.,Cvetovich, Raymond J.,Gong, Xiaoyi,McLaughlin, Mark,Reamer, Robert A.
, p. 1930 - 1933 (2005)
(Chemical Equation Presented) 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 tetrabutyl-ammonium 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 butyl group on the nitrogen is efficiently generated through the addition of methylmagnesium chloride to a dimethyliminium salt in 71% overall yield.
