反应详情

To a solution of 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzonitrile (0.24 g, 0.63 mmol) in toluene (5 mL) were added dibutyltin oxide (0.025 g, 0.1 mmol) and trimethylsilyl azide (0.15 g, 1.26 mmol). The reaction mixture was heated for 60 hours. The mixture was then cooled to room temperature and concentrated under vacuum. The residue was dissolved in methanol (5 mL) and then concentrated. The residue was partitioned between saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate. The aqueous layer was washed with ethyl acetate (3×10 mL). The combined extracts were dried (MgSO4) and concentrated. Purification by flash chromatography with CH2Cl2/MeOH (9:1) afforded 0.19 g (71% yield) of 1-Benzyl-4-(3-methoxy-phenyl)4-[4-(1H-tetrazol-5-yl)-phenyl]-piperidine. 1HNMR (400 MHz, CD3OD) δ 7.95 (d, 2H), 7.44-7.41 (comp, 7H), 7.23-7.18 (m, 1H), 6.90-6.77 (comp, 2H), 6.76 (d, 1H), 6.70 (d, 1H), 4.21 (s, 2H), 3.64 (s, 3H), 3.30-2.41 (comp, 8H); MS (M+1) 426.2.

1. temperatureThe reaction mixture was heated for 60 hours
2. concentrationconcentrated under vacuum
3. dissolutionThe residue was dissolved in methanol (5 mL)
4. concentrationconcentrated
5. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate
6. washThe aqueous layer was washed with ethyl acetate (3×10 mL)
7. dry with materialThe combined extracts were dried (MgSO4)
8. concentrationconcentrated
9. customPurification by flash chromatography with CH2Cl2/MeOH (9:1)