2-Bromo-N-(2-Bromoethyl)-N-Carbethoxyethanamine, a Useful Reagent in the Synthesis of 4,4 Disubstituted Piperidines

Abstract

With this we like to communicate on the use of the reagent, 2-bro-mo-N-(2-bromoethyl)-N-carbethoxyethanamine 1, in the synthesis of 4,4 disubstituted piperidines. The latter are of interest in the field of neuroleptics¹, local anesthetics², analgetics^3,4 and antidiarrhoeal agents⁵. Synthesis of some of them can be realized starting from an appropriate 4-functionalized piperidine¹. A method using the alkylation of active methylene compounds with N-mustard derivatives of type 2a,b is most useful^2-4,6. Also the N-sulfonyl protected derivative 2c has been used, with variable success; however if refunctionalization on the piperidine N-atom is required, the sulfonyl group is not easily removed.