Triethylamine → HCID 57890442, compound

Participants

Reaction Steps

To a solution of 4-bromobenzylamine hydrochloride (971 mg, 4.37 mmol), [4-(bromomethyl)phenyl]acetic acid (1.00 g, 4.37 mmol), 1-hydroxybenzotriazole (590 mg, 4.37 mmol) and triethylamine (668 μl, 4.80 mmol) in dimethylformamide (11 ml) was added ethyldimethylaminopropylcarbodiimide hydrochloride (837 mg, 4.37 mmol) at 0° C., and the mixture was stirred at room temperature 16 hrs. Ethyl acetate was added to the reaction mixture. The mixture was washed with aqueous potassium carbonate solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate), and powderized with ethyl acetate-isopropyl ether (1:5). A solution of the obtained powder (850 mg, 2.24 mmol), pyrrolidine (561 μl, 6.37 mmol) and potassium carbonate (930 mg, 6.37 mmol) in dimethylformamide (10 ml) was stirred at 80° C. for 16 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate), and powderized with isopropyl ether to give the title compound (437 mg).

Provenance & Evidence