Methanol → HCID 22485555, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen, lithium aluminum hydride (4.28 g, 113 mmol) was added to an ice-cold solution of N,N-bis[2-[N-[2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]-5-pyridyl]carbamoyl]ethyl]methylamine (22.50 g, 28.3 mmol) in anhydrous tetrahydrofuran (500 mL). The ice bath was removed, and the reaction mixture was stirred at 65° C. for 1 hour. Methanol (20 mL, 490 mmol) was added to the ice-cold reaction mixture, and the ice bath was removed. Water (20 mL), diethyl ether (2 L), and anhydrous magnesium sulfate (130 g) were added, and the mixture was stirred overnight at room temperature. Insoluble materials were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide N,N-bis[N-[2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]-5-pyridyl]-3′-aminopropyl]methylamine as a colorless oil (20.32 mg, yield: 94%).

Provenance & Evidence