反应详情

温度

100 °C

3-Fluoro-N-(4-formyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide (100 mg, 264 μmol) in morpholine (2.5 ml) is heated to 100° C. for 2.5 hours. Sodium cyanoborohydride (200 mg) is then added and the mixture heated at 100° C. for an additional 2 hours. The mixture is cooled to room temperature poured into ethyl acetate (100 ml), washed with water (2×50 ml) and brine (50 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by column chromatography on silica gel eluting with 70% ethyl acetate in hexanes to give product as a white solid (64 mg). Mp: 192-3° C. 1H NMR 400 MHz (CDCl3) δ 8.32 (m, 1H), 8.03 (s, 1H), 7.83 (m, 2H), 7.5 (m, 2H), 7.39 (d, 1H, J=7.6 Hz), 7.24 (s, 1H), 6.98 (d, 1H, J=8 Hz), 6.70 (d, 1H, J=11.6 Hz), 3.8 (m, 6H), 3.62 (t, 4H, J=4.4 Hz), 3.19 (t, 4H, J=4.8 Hz), 2.45 (s, 4H). MS: 450 (M+1).

1. temperatureThe mixture is cooled to room temperature
2. washwashed with water (2×50 ml) and brine (50 ml)
3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
4. customevaporated to dryness
5. customThe residue is purified by column chromatography on silica gel eluting with 70% ethyl acetate in hexanes