6-(Piperidin-1-yl)pyridine-3-carbaldehyde → 3-(4-sec-butylphenyl)-2-(6-(piperidin-1-yl)pyridin-3-yl)quinazolin-4(3H)-one

Participants

Reaction Steps

2-amino-N-(4-sec-butylphenyl)benzamide (0.350 g, 1.3 mmol) and 6-(piperidin-1-yl)nicotinaldehyde (1.3 mmol) were mixed in anyhydrous EtOH (40 mL) and anyhydrous CuCl2 (0.524 g, 3.9 mmol) was added. The reaction mixture was heated at reflux for 3 hours, cooled to room temperature, and stirred overnight. The reaction mixture was concentrated, diluted with ethyl acetate (150 mL), washed with water (2×100 mL), dried (MgSO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 80% ethyl acetate/heptane, afforded the title compound as a white solid (35%) as a white solid. 1H-NMR (300 MHz, DMSO-d6): δ 8.14-8.17 (m, 1H), 8.05 (d, J=2.4 Hz, 1H), 7.85-7.90 (m, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.53-7.58 (m, 1H), 7.35 (d, J=6.5 Hz, 1H), 7.17-7.24 (m, 4H), 6.55 (d, J=9.1 Hz, 1H), 3.40-3.49 (m, 4H), 2.57-2.66 (m, 1H), 1.44-1.64 (m, 8H), 1.19 (d, J=6.9 Hz, 3H), 0.68 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 439 (M+H)+.

Provenance & Evidence