A mixture of 3-methyl-4-(2-oxoethyl)benzonitrile (130 mg, 0.8 mmol), 1-[2-(4-nitrophenyl)ethyl]piperazine (188 mg, 0.8 mmol) and NaBH(OAc)3 in 25 mL of dry methanol were stirred at room temperature over night. The solid was filtered to get 160 mg of 3-methyl-4-((E)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}vinyl)benzonitrile. 1H-NMR (300 MHz, CDCl3) δ ppm 8.15 (d, J=8.6 Hz, 2H), 7.31˜7.40 (m, 5H), 6.72 (d, J=13.5 Hz, 1H), 5.35 (d, J=13.9 Hz, 1H), 3.20 (s, 4H), 2.95 (s, 2H), 2.57˜2.75 (m, 6H), 2.26 (s, 3H). MS m/z: 377 (M+1)+.
