o-Chlorophenylacetic acid → 4-(2-Bromo-5-hydroxybenzyl)-1-[(2-chlorophenyl)acetyl]piperidine

Participants

Reaction Steps

In N,N-dimethylformamide (10 ml) were dissolved 4-(2-bromo-5-hydroxybenzyl)piperidine (the compound of Example 10) (2010.9 mg, 7.500 mmol), 2-chlorophenylacetic acid (1279.5 mg, 7.500 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1716.3 mg, 9.000 mmol) and 1-hydroxybenzotriazole (1114.8 mg, 7.500 mmol), and the resulting solution was stirred at room temperature for 5 hours. The reaction was terminated by adding water (100 ml), followed by extraction with a toluene-diethyl ether mixture (1:1). The organic layer was washed successively with a 5% aqueous sodium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent, whereby the title compound (2754.4 mg, 6.547 mmol) was obtained in a yield of 87%.

Provenance & Evidence