反应详情

温度

90 °C

A mixture of 2-[(1S)-3-chloro-1-phenylpropyl]-1H-isoindole-1,3(2H)-dione (4.50 g, 15.0 mmol), 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide (4.26 g, 15.0 mmol), K2CO3 (4.16 g, 30.0 mmol), and NaI (3.40 g, 20.0 mmol) in DMF (40 mL) was stirred at 90° C. for 12 hrs. The reaction mixture was diluted with water (50 mL), extracted with CH2Cl2 (3×50 mL), and the combined organic extracts were washed with brine (50 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica using 5% of NH3 (2.0 M in methanol) in CH2Cl2 to give the desired product (5.10 g, 74%). 1H NMR (400 MHz, CDCl3) δ 7.83 (d, 1H, J=5.5 Hz), 7.82 (d, 1H, J=5.5 Hz), 7.71 (d, 1H, J=5.5 Hz), 7.70 (d, 1H, J=5.4 Hz), 7.56 (d, 2H, J=7.1 Hz), 7.35–7.27 (m, 5H), 7.22 (t, 1H, J=7.5 Hz), 7.09 (s, 1H), 6.81 (d, 1H, J=7.8 Hz), 5.49 (dd, 1H, J=5.5, 9.6 Hz), 2.97 (d, 1H, J=10.1 Hz), 2.92–2.82 (m, 2H), 2.44 (sept, 1H, J=6.7 Hz), 2.40–2.29 (m, 3H), 2.00–1.83 (m, 2H), 1.79–1.39 (m, 5H), 1.26 (d, 6H, J=6.9 Hz); ESMS m/e: 510.4 (M+H)+.

1. extractionextracted with CH2Cl2 (3×50 mL)
2. washthe combined organic extracts were washed with brine (50 mL)
3. dry with materialdried over MgSO4
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by chromatography on silica using 5% of NH3 (2.0 M in methanol) in CH2Cl2