Triethylamine → HCID 66731694, compound

Participants

Reaction Steps

Dimethyl 2-(4-(methylsulfonyl)phenyl)piperidine-1,4-dicarboxylate (5.952 g, 16.75 mmol) was dissolved in acetonitrile (50 mL) and water (1.000 mL), then lithium bromide (11.64 g, 133.98 mmol) added. Triethylamine (9.29 mL, 66.99 mmol) was added and the reaction mixture heated under reflux for 1.5 h. MTBE (150 mL) and water (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 to pH 1 with 3 M HCl and extracted with MTBE (2×500 mL). The combined organic phases were dried with Na2SO4, filtered and evaporated in vacuo yielding 1-(methoxycarbonyl)-2-(4-(methylsulfonyl)phenyl)piperidine-4-carboxylic acid (4.76 g, 83%). MS m/z 342 (M+H)+

Provenance & Evidence