Ethanol → [1-(3-Chloro-benzyl)-1H-[1,2,4]triazol-3-yl]-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-yl]-amine

Participants

Reaction Steps

A solution of 1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one (91 mg, 0.5 mmol) and 1-(3-chloro-benzyl)-1H-[1,2,4]triazol-3-ylamine (104 mg, 0.5 mmol) in dry toluene (8 mL) and acetic acid (0.4 mL) was heated under reflux at a Dean-Stark trap for 12 hours. The reaction mixture was cooled to room temperature, ethanol (5 mL) was added, followed by sodium borohydride (19 mg, 0.5 mmol) and stirred at room temperature overnight. The reaction mixture was extracted with water and ethyl acetate, the organic layers were combined, dried over Na2SO4, filtered and the solvents were evaporated. The residue was purified by silica gel chromatography using dichloromethane/methanol as eluent. The title compound was obtained as a white solid (91 mg, 49%).

Provenance & Evidence