3-(Trifluoromethoxy)benzaldehyde → [1-(3-Trifluoromethoxy-benzyl)-piperidin-4-yl]-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine

Participants

Reaction Steps

A mixture of piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine (D4) (0.025 g, 0.10 mmol), 3-trifluoromethoxy-benzaldehyde (0.034 ml, 0.29 mmol) and polymer supported triacetoxyborohydride (2.07 mmol/g) (0.165 g, 0.29 mmol) in 1,2-dichloroethane (2 ml) was shaken at room temperature for 16 h. After this period, the reaction mixture was filtered through an Isolute SCX-2 cartridge. The cartridge was washed with methanol. The crude product was eluted with a 7M solution of ammonia in methanol. The solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 5% ammonia in methanol (7M)/dichloromethane) to yield E13 (0.029 g, 68%) as a white solid. C16H16F6N4OS requires 426. Found 427 (MH+).

Provenance & Evidence