反应详情

2-amino-N-(4-chlorophenyl)benzamide (0.318 g, 1.3 mmol) and 6-(piperidin-1-yl)nicotinaldehyde (1.3 mmol) were mixed in anhydrous EtOH (40 mL) and anhydrous CuCl2 (0.524 g, 3.9 mmol) was added. The reaction mixture was heated at reflux for 5 hours, cooled to room temperature, and stirred overnight. The reaction mixture was concentrated, diluted with ethyl acetate (150 mL), washed with water (2×100 mL), dried (MgSO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 75% ethyl acetate/heptane, afforded the title compound as a white solid (35%). 1H-NMR (300 MHz, DMSO-6): δ 8.16 (d, J=8.0 Hz, 1H), 8.11 (d, J=2.4 Hz, 1H), 7.86-7.91 (m, 1H), 7.74 (d, J=8.0 Hz, 1H), 7.54-7.59 (m, 1H), 7.36-7.50 (m, 5H), 6.64 (d, J=9.0 Hz, 1H), 3.49-3.53 (m, 4H), 1.48-1.58 (m, 6H). MS (APCI) m/z: 417 (M+H)+.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 5 hours
3. concentrationThe reaction mixture was concentrated
4. additiondiluted with ethyl acetate (150 mL)
5. washwashed with water (2×100 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. washFlash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 75% ethyl acetate/heptane