Sodium triacetoxyborohydride → 2-(Methylamino)-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

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Reaction Steps

A solution of crude 2-(methylamino)-4-(2-piperazin-1-ylethyl)benzonitrile (˜18 mg, 0.05 mmol), (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (9 mg, 0.05 mmol) and NaBH(OAc)3 (100 mg, 0.47 mmol) in 10 mL of anhydrous DCM was stirred at ambient temperature overnight. The reaction mixture was added 50 mL of DCM and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford 2-(methylamino)-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ 7.77 (d, J=7.8, 1H), 7.22˜7.32 (m, 3H), 6.42˜6.47 (m, 2H), 5.22 (s, 2H), 4.50˜4.58 (m, 1H), 2.84˜2.91 (m, 7H), 2.72˜2.77 (m, 2H), 2.53˜2.67 (m, 10H). (0.43 μM)

Provenance & Evidence