反应详情

温度

120 °C

A mixture of {4-[4-(3-cyanopropoxy)phenyl]butyl}carbamic acid benzyl ester 2 (0.90 g, 2.5 mmol), sodium azide (0.50 g, 7.5 mmol), and ammonium chloride (0.40 g, 7.5 mmol) in DMF (7 mL), was stirred at 120° C. for 16 h. Inorganics were removed by vacuum filtration. The filtrate was diluted with ethyl acetate, and washed with water and brine. The organic solution was dried over Na2SO4, filtered and concentrated. The residue was taken up in ethyl acetate (5 mL) and diluted with hexanes (10 mL). Solid precipitates were collected by suction filtration and purified by flash silica gel column chromatography eluting with methanol/dichloromethane (1:50, v/v) to give the desired product 3 as a white solid (0.78 g, 76% yield). 1H NMR (300 MHz, CD3OD) δ 1.51 (m, 4H), 2.20 (m, 2H), 2.50 (m, 2H), 3.10 (m, 4H), 4.00 (m, 2H), 5.00 (s, 2H), 6.75 (d, 2H), 7.05 (d, 2H), 7.30 (m, 5H). m/z (ESI): 410 [C22H27N5O3+H]+.

1. customInorganics were removed by vacuum filtration
2. additionThe filtrate was diluted with ethyl acetate
3. washwashed with water and brine
4. dry with materialThe organic solution was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. additiondiluted with hexanes (10 mL)
8. customSolid precipitates
9. filtrationwere collected by suction filtration
10. custompurified by flash silica gel column chromatography
11. washeluting with methanol/dichloromethane (1:50