Chlorosuccinimide → 1-(4-Chloromethyl-5-methyl-1,3-thiazol-2-yl)piperidine

Participants

Reaction Steps

To a solution of 1-(4,5-dimethyl-1,3-thiazol-2-yl)piperidine (4.00 g) in acetonitrile (100 mL) was added N-chlorosuccinimide (2.72 g) at room temperature, and the mixture was stirred at the same temperature for 15 hrs. After concentration of the reaction mixture, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 1-(4-chloromethyl-5-methyl-1,3-thiazol-2-yl]piperidine as colorless crystals (0.67 g, yield 14%) from a fraction eluted with ethyl acetate-hexane (1:8, v/v). Recrystallization from ethyl acetate-hexane gave colorless needle crystals. melting point: 79-80° C.

Provenance & Evidence