3-Fluorobenzyl bromide → [1-(3-Fluoro-benzyl)-piperidin-4-yl]-methyl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl-piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine (D2) (0.050 g, 0.19 mmol), 3-fluorobenzyl bromide (0.030 ml, 0.24 mmol) and diisopropylethylamine (0.050 ml, 0.28 mmol) in acetonitrile (3 ml) was stirred at 100° C. for 5 min., under microwave irradiation. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and extracted with a 10% solution of ammonium chloride (25 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 0-1.5% ammonia in methanol (7M)/dichloromethane) to yield E2 (0.062 g, 88%) as a solid. C16H18F4N4S requires 374. Found 375 (MH+).

Provenance & Evidence