Ethyl bromoacetate → [4-(4-Chloro-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of (4-chloro-phenyl)-piperidin-4-yl-methanone (1.0 g, 3.8 mmol) and bromo-acetic acid ethyl ester (0.71 g, 4.2 mmol) in acetonitrile (10 mL) was added triethylamine (0.78 g, 7.7 mmol), the reaction mixture was stirred at 85° C. for 15 h. The reaction mixture was cooled to ambient temperature, the solvent was removed, the residue was redissolved in DCM (20 mL), washed with water (20 mL), the organic layers were then washed with brine (20 mL) and dried over Na2SO4. Purification by flash chromatography gave the title compound as a white solid (1.01 g, 3.10 mmol, 81% yield). MS (ESI) m/z 310.3 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.45 min.

Provenance & Evidence