Ethyl bromoacetate → [4-(2-Trifluoromethoxy-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of piperidin-4-yl-(2-trifluoromethoxy-phenyl)-methanone in 5 mL of acetonitrile was added Et3N (0.3 mL, 2.4 mmol, 2 eq.), followed by ethyl 2-bromoacetate (0.14 mL, 1.3 mmol, 1.1 eq.) added dropwise and heated at 85° C. overnight. After 18 h, the reaction mixture was concentrated in vacuo, diluted with saturated NaHCO3 (100 mL) and extracted with ethyl acetate (3×50 mL). The combine organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give a dark oil. This oil was purified by silica gel column chromatography (30-50% ethyl acetate/heptane) to give the title as a light brown oil (0.36 g, 85%). Exact mass calculated for C18H22F3N1O4 360.1. MS (ESI) m/z 360.7 (M+H)+.

Provenance & Evidence