反应详情

To a solution of 2-(diphenylmethyleneamino)acetonitrile (1.21 g, 5.47 mmol, 1.0 equiv) in CH2Cl2 (9.12 mL) was added 4-fluorobenzyl bromide (0.75 mL, 6.02 mmol, 1.1 equiv), benzyltrimethylammonium chloride (0.10 g, 0.547 mmol, 0.1 equiv), and NaOH (0.99 mL of a 10 M aqueous solution, 9.85 mmol, 1.8 equiv). The reaction was stirred vigorously for 18 h, at which time TLC analysis indicated complete consumption of the starting nitrile. The reaction was added to water and extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by silica gel chromatography (5-30% ethyl acetate/hexane) to provide the title compound (1.65 g, 92% yield) as a viscous yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.54-7.65 (m, 2H), 7.38-7.48 (m, 4H), 7.31-7.38 (m, 2H), 7.00-7.09 (m, 2H), 6.89-6.97 (m, 2H), 6.84 (d, J=6.30 Hz, 2H), 4.35 (dd, J=7.81, 6.04 Hz, 1H), 3.10-3.29 (m, 2H); LCMS (ES+, (M+H)+) m/z 329.25.

1. customconsumption of the starting nitrile
2. additionThe reaction was added to water
3. extractionextracted with CH2Cl2 (×3)
4. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe crude product was purified by silica gel chromatography (5-30% ethyl acetate/hexane)