反应详情

To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) in MeOH (5 mL) was added solid sodium tungstate dihydrate (332 mg, 1.0 mmol) followed by a 35 wt % aqueous solution of hydrogen peroxide (2.9 mL, 30 mmol). The resulting suspension was stirred 3 h, then saturated aqueous sodium bicarbonate (5 mL) was added. The phases were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL), then the combined organic extracts were washed once with brine (10 mL), dried (MgSO4), and concentrated in vacuo. Purification of the crude material by flash chromatography (silica gel, 75:1:1 CH2Cl2MeOH/NH4OH) afforded the title compound (130 mg, 63%) as a white solid. 1H NMR (CDCl3) δ 1.63–1.66 (m, 1H), 1.97–2.07 (m, 2H), 2.25–2.27 (m, 1H), 2.66–2.72 (m, 1H), 2.80–2.85 (m, 1H), 3.65 (d, 1H, J=14 Hz), 3.71 (d, 1H, J=14 Hz), 5.03 (d, 1H, J=16 Hz), 4.14 (dd, 1H, J=9, 7 Hz), 4.21 (d, 1H, J=16 Hz), 7.11–7.19 (m, 3H), 7.41–7.48 (m, 6H), 7.65 (br d, 1H, J=5 Hz), 8.18 (s, 1H), 8.67 (dd, 1H, J=5, 1 Hz); 13C NMR (CDCl3) δ 22.2, 23.9, 30.2, 49.5, 55.0, 61.2, 112.1, 119.4, 122.7, 123.3, 127.8, 130.1, 133.0, 136.2, 138.7, 141.4, 147.8, 150.0, 156.2, 157.7. ES-MS m/z 412 (M+H). Anal. Calcd. for C25H25N5O.0.4H2O.0.3CH2Cl2: C, 68.41; H, 5.99; N, 15.77. Found: C, 68.57; H, 5.86; N, 15.48.

1. customThe phases were separated
2. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
3. washthe combined organic extracts were washed once with brine (10 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customPurification of the crude material by flash chromatography (silica gel, 75:1:1 CH2Cl2MeOH/NH4OH)