Acetonitrile → HCID 66732298, compound

Participants

Reaction Steps

Dimethyl 2-(4-chlorophenyl)piperidine-1,4-dicarboxylate (3.97 g, 12.73 mmol) was dissolved into acetonitrile (55 mL) and water (1.1 mL), then lithium bromide (8.85 g, 101.87 mmol) was added. Et3N (7.10 mL, 50.94 mmol) was added and the resulting yellow suspension was heated at reflux for 2 h. Water (100 mL) and MTBE (150 mL) were added. The phases were separated and the organic layer was extracted with water (2×). The pooled water layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE (2×). The combined organic layer was dried over Na2SO4, filtered and evaporated leaving 2-(4-chlorophenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (3.49 g, 92%) as a yellow semi-solid. MS m/z 298 (M+H)+

Provenance & Evidence