Acetic Acid → 2-Chloro-4-(2-{2-oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

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Reaction Steps

A mixture of 2-Chloro-4-[2-(2-oxopiperazin-1-yl)ethyl]benzonitrile (70 mg, 0.265 mmol), (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (82 mg, 0.466 mmol), NaBH3CN (43 mg, 0.68 mmol) and acetic acid (28 mg, 0.466 mmol) in methanol (2 mL) and DCM (2 mL) was stirred at RT for 3 hours. Then the mixture was purified by prep-TLC to give the title product. 1H-NMR (MeOD, 400 MHz) δ ppm 7.83 (d, J=7.6 Hz, 1H), 7.71 (d, J=7.6 Hz, 1H), 7.58 (d, J=1.6 Hz, 1H), 7.54 (s, 1H), 7.50 (d, J=7.6 Hz, 1H), 7.38 (dd, J=1.6, 7.6 Hz, 1H), 5.36 (s, 2H), 3.78 (s, 2H), 3.68 (t, J=7.2 Hz, 2H), 3.56 (t, J=5.6 Hz, 2H), 3.40-3.42 (m, 2H), 3.30-3.33 (m, 2h), 3.13-3.18 (m, 2H), 2.98 (t, J=7.6 Hz, 2H).

Provenance & Evidence