Two efficient routes to 1-tert-butyl-4-chloropiperidine aredescribed. 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 tertiarybutyl group on the nitrogen is efficiently generated throughthe addition of methylmagnesium chloride to a dimethyliminium salt in 71% overall yield.