2-Amino-N-(4-sec-butylphenyl)benzamide → HCID 46842008, compound

Participants

Reaction Steps

2-amino-N-(4-sec-butylphenyl)benzamide (0.250 g, 0.92 mmol) and 6-((tetrahydro-2H-pyran-2-yloxy)methyl)nicotinaldehyde (0.77 mmol) were mixed in anyhydrous EtOH (40 mL) and anyhydrous CuCl2 (0.310 g, 2.3 mmol) was added. After heating at reflux for 1.5 hours, and concentrating, ethyl acetate (150 mL) was added, the mixture was washed with water (2×125 mL), dried (MgSO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 50% ethyl acetate/heptane to 100% ethyl acetate, plus re-chromatographing with 30% ethyl acetate/CH2Cl2 to 100% ethyl acetate, afforded the title compound as a white solid (40%). 1H-NMR (300 MHz, DMSO-6): δ8.47 (d, J=1.6 Hz, 1H), 8.21 (d, J=7.8 Hz, 1H), 7.89-7.94 (m, 1H), 7.79 (d, J=7.9 Hz, 1H), 7.60-7.72 (m, 2H), 7.26-7.29 (m, 3H), 7.14-7.18 (m, 2H), 5.42 (t, J=5.8 Hz, 1H), 4.45 (d, J=5.7 Hz, 2H), 2.55-2.64 (m, 1H), 1.37-1.58 (m, 2H), 1.15 (d, J=6.9 Hz, 3H), 0.64 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 386 (M+H)+.

Provenance & Evidence