反应详情

4-Chlorophenylacetylchloride (106 mg, 0.56 mmol) in dichloromethane was added to a solution of 3-acetyl-α, α-dimethylbenzylamine 24 (100 mg, 0.56 mmol) and triethylamine (120 μL, 0.86 mmol) in dichloromethane over a period of 5 to 10 min at 0° C. The reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane (20 mL) and washed with 1 N HCl, water and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by column chromatography using hexane/ethyl acetate as eluent to give 26 (146 mg, 80%). 1H NMR (CDCl3, 400 MHz) δ 1.61 (s, 6H), 2.53 (s, 3H), 3.46 (s, 2H), 5.68 (s, 1H), 7.19 (d, J=7.2 Hz, 2H), 7.30-7.38 (m, 3H), 7.46 (d, J=8 Hz, 1H), 7.75 (d, J=7.2 Hz, 1H), 7.87 (s, 1H); 13C NMR (DMSO-d6 100 MHz) δ 27.26, 29.89, 42.54, 55.34, 124.71, 126.76, 128.74, 128.98, 130.23, 131.45, 131.63, 136.22, 137.19, 148.96, 169.54, 198.59; ESI-HRMS for C19H21NO2Cl (M+H)+ calcd. 330.1261. found 330.1270.

1. washwashed with 1 N HCl, water and brine
2. dry with materialThe organic layer was dried over anhydrous MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customThe residue was purified by column chromatography