Acetonitrile → HCID 66732454, compound

Participants

Reaction Steps

Dimethyl 2-(4-chloro-2-fluorophenyl)piperidine-1,4-dicarboxylate (7.77 g, 23.56 mmol) was dissolved into acetonitrile (100 mL) and water (2.000 mL), then lithium bromide (16.37 g, 188.51 mmol) was added. Et3N (13.14 mL, 94.25 mmol) was added and the resulting yellow suspension was heated under reflux for 2 h. Water (200 mL) and MTBE (300 mL) were added. The phases were separated and the organic layer was extracted with water (2 times). The pooled water layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE (2 times). The combined organic layer was dried over MgSO4, filtered and evaporated yielding 2-(4-chloro-2-fluorophenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (7.28 g, 98%) as a yellow semi-solid. MS m/z 316 (M+H)+

Provenance & Evidence