Piperidine → HCID 9968042, compound

Participants

Reaction Steps

A mixture of 4,5-diphenyl-I-methylimidazole-2-carboxylic acid (50 mg, 0.18 mmol) from Step A, 1-aminopiperidine (0.052 mL, 0.36 mmol) (containing a small percent of piperidine as an impurity), PyBOP (NovaChem) (140 mg, 0.2 mmol) and N,N-diisopropyl-N-ethylamine (DIPEA) (0.065 mL, 0.2 mmol) in methylene chloride (2 mL) was stirred at rt for 20 hr. The reaction was diluted with water and extracted twice with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified twice by prep TLC (1 mm, silica gel) eluting with 5% methylene chloride, 35% ethyl acetate in hexanes to afford the primary product N-(piperidin-1-yl)-4,5-diphenyl-1-methylimidazole-2-carboxamide and 2-(piperidin-1-ylcarbonyl)-4,5-diphenyl-1-methylimidazole as a byproduct. HPLC/MS: 361 (M+1); Rt=2.64 min; 1HNMR (CDCl3): 1.4–1.7 (m, 2H), 1.92 (m, 4H), 2.96 (br s, 4H), 3.90 (s, 3H), 7.24 (m, 3H), 7.34 (m, 2H), 7.50 (m, 5H).

Provenance & Evidence