Triethylamine → N-[2-(3-cyanophenoxy)ethyl]-4-[(pyridine-4-yl)methyl]benzamide

Participants

Reaction Conditions

Reaction Steps

262 mg (1.15 mmol) of methyl 4-[(pyridine-4-yl)methyl]benzoate was dissolved in 5 ml of concentrated hydrochloric acid. The solution was stirred at 70° C. for 15 hours. The solvent was evaporated, and the residue was dissolved in 5 ml of dichloromethane. 0.24 ml (1.73 mmol) of triethylamine, 243 mg (1.27 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 172 mg (1.27 mmol) of 1-hydroxybenzotriazole and 308 mg (1.27 mmol) of 3-(2-aminoethoxy)benzonitrile hydrochloride were added to the solution, and they were stirred for 15 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Provenance & Evidence