反应详情

Sodium perborate tetrahydrate (221 mg, 1.43 mmol) and glacial acetic acid (5 ml) was heated to 50 to 60° C. and 4-[4-(3-Thiomorpholin-4-ylpropoxy)phenyl]tetrahydropyran-4-carbonitrile (500 mg, 1.43 mmol) was added in one portion and the heating was maintained for 3 hours. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was added to ice water (15 ml) and extracted with EtOAc (3×5 ml), which was discarded. The aqueous phase was basified to pH 8-9 with 2M sodium hydroxide and extracted with DCM (3×25 ml), dried over MgSO4, filtered and concentrated in vacuo at 35° C. The crude material was subjected to chromatography on silica eluting with DCM:MeOH:NH3 (97:2:1 to 92:6:2) to provided the title compound (300 mg, 58%) as a white solid. 1H NMR (400 MHz, CDCl3), δ 7.38 (d, 2H), 6.92 (d, 2H), 4.11-4.05 (m, 2H), 4.03 (t, 2H), 3.89 (td, 2H), 3.15-3.03 (m, 2H), 2.94-2.67 (m, 6H), 2.63 (t, 2H), 2.16-1.92 (m, 6H).

1. temperaturethe heating was maintained for 3 hours
2. filtrationfiltered
3. additionThe filtrate was added to ice water (15 ml)
4. extractionextracted with EtOAc (3×5 ml), which
5. extractionextracted with DCM (3×25 ml)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo at 35° C