Ammonium Chloride → HCID 178482464, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (26.0 g) in ethanol (100 mL) were added 4-imino-1-methyl-3-(phenylcarbonyl)imidazolidin-2-one (16.7 g) and potassium tert-butoxide (8.60 g) under ice-cooling. The reaction mixture was stirred at 80° C. for 2 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution at room temperature, and ethanol was evaporated under reduced pressure. Water and ethyl acetate were added to the residue, and the insoluble material was collected by filtration, recrystallized from ethanol/water, and further recrystallized from acetone/water. To a solution of the obtained solid (2.03 g) in toluene (10 mL) was added a solution (4.8 mL) of methylamine in 40% methanol at room temperature. The reaction mixture was stirred at 70° C. overnight, 40% methanol solution (4.8 mL) was added at room temperature, and the mixture was stirred at 70° C. overnight. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) and recrystallized from ethyl acetate/heptane to give the title compound (1.10 g).

Provenance & Evidence