Methyl chloroformate → HCID 21465533, compound

Participants

Reaction Steps

To a solution of a 4-amino-1-phenethyl-piperidine hydrochloride (Example 8c, 2 g, 0.0072 Mol) and triethylamine (3.31 ml, 3.3 Mol eq) in dichloromethane (30 ml) was added 2-bromopropiophenone (1.54 g, 1 Mol eq) and the reaction mixture was stirred for 14 h at room temperature. After ice-bath cooling, methylchloroformate (3.36 ml, 6 Mol eq) was added and the reaction mixture stirred for a further 1 h. Triethylamine (5 ml) was added and the reaction mixture was concentrated in vacuo. The residue was redissolved in methanol (50 ml) and sodium methoxide (3 g) was added. After stirring at room temperature for 0.5 h, the reaction mixture was heated under reflux for 1h. After cooling, the solution was concentrated under vacuum and the residue obtained was partitioned between dichloromethane and water then dried (MgSO4), filtered and evaporated. The crude product was purified on a silica gel column using 0 to 2% methanol in dichloromethane as eluent then recrystallised from diethyl ether/hexane to give the title compound as a colourless solid (0.14 g, 5%). Mp 144° C. 1H NMR (DMSO) δ 1.72 (2H, m), 2.08 (2H, m), 2.30 (3H s), 2.33 (2H, m), 2.50 (2H, m), 2.75 (2H, m), 3.04 (2H, s), 3.69 (1H, m), 7.16-7.33 (5H, m), 7.42-7.47 (5H, m); MS (CI) m/e 363 [MH]+. Anal. Found C, 76.10; H, 7.19; N, 7.61. C23H26 ClN3O. 0.35H2O requires C, 76.21; H, 7.23; N, 7.73%.

Provenance & Evidence