Sodium Hydroxide → N-(3-Bromo-4-fluorobenzyl)tetrahydro-2H-thiopyran-4-amine

Participants

Reaction Steps

To a solution of tetrahydro-4H-thiopyran-4-one (1.16 g) in chloroform (50 mL), 3-bromo-4-fluorobenzylamine (2.41 g) was added and the resulting mixture was stirred at room temperature for an hour. Sodium (triacetoxy)borohyride (6.36 g) was added and the resulting mixture was stirred overnight. To the reaction mixture, an aqueous solution of 2 M sodium hydroxide was added and after stirring the resulting mixture, extraction was performed with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure and the resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=100:0 to 99:1) to give the titled compound (1.72 g).

Provenance & Evidence