Triethylamine → HCID 66732169, compound

Participants

Reaction Steps

Dimethyl 2-(3,4,5-trifluorobenzyl)piperidine-1,4-dicarboxylate (4.01 g, 11.61 mmol) was dissolved in acetonitrile (40 mL) and water (0.8 mL). Lithium bromide (2.329 mL, 92.90 mmol) was added followed by triethylamine (6.44 mL, 46.45 mmol). The reaction was refluxed for 2 h. The reaction was cooled to room temperature. Water (200 mL) and MTBE (150 mL) were added, shaken and the phases separated. The organic phase was extracted with water (2×150 mL). The combined aqueous phases were acidified with 3 M HCl to pH 1 and then extracted with MTBE (2×400 mL). The combined organic phases were dried with Na2SO4, filtered and evaporated in vacuo to yield 1-(methoxycarbonyl)-2-(3,4,5-trifluoro-benzyl)piperidine-4-carboxylic acid (3.42 g, 89%) as a light brown foam. MS m/z 330 (M−H)−

Provenance & Evidence