Triethylamine → HCID 23090937, compound

Participants

Reaction Steps

To a solution of 4-(cyclopropylmethoxy)-2-fluorobenzoic acid (242 mg, 1.15 mmol) and dimethylformamide (1 drop) in tetrahydrofuran (3 ml) was added dropwise oxalyl dichloride (113 μl, 1.30 mmol) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure and the obtained residue was dissolved in tetrahydrofuran (3 ml). The solution was added dropwise to a solution of 2-{4-[1-(1-piperidinyl)ethyl]phenyl}ethylamine (310 mg, 1.02 mmol) obtained in Reference Example 15 and triethylamine (558 μl, 4.00 mmol) in tetrahydrofuran (2 ml) at 0° C., and the mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture. The mixture was extracted with ethyl acetate, and the extract 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) to give the title compound (200 mg).

Provenance & Evidence