Triethylamine → 2-(4-Chloro-3-fluorophenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

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Reaction Steps

Dimethyl 2-(4-chloro-3-fluorophenyl)piperidine-1,4-dicarboxylate (1.625 g, 4.93 mmol) was dissolved in acetonitrile (20 mL) and water (0.400 mL). lithium bromide (3.42 g, 39.42 mmol) was added. Triethylamine (2.73 mL, 19.71 mmol) was then added and the reaction heated under reflux for 1.5 h. Water (200 mL) and MTBE (150 mL) were added, shaken and the phases separated. The organic phase was extracted with water (2×200 mL). The combined aqueous phases were acidified with 3 M HCl to pH 1 and then extracted with MTBE (2×500 mL). The combined organic phases were dried with Na2SO4, filtered and evaporated in vacuo yielding 2-(4-chloro-3-fluorophenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (1.430 g, 92%). MS m/z 314 (M−H)−

Provenance & Evidence