4-Cyclohexylbenzenamine → HCID 46841138, compound

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Reaction Steps

Following the method described for Example 21, 2-amino-N-(4-cyclohexylphenyl)benzamide was made from 4-cyclohexylaniline in 70% yield and isolated as a white solid. 2-Amino-N-(4-cyclohexylphenyl)-benzamide (4.58 mmol), 4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylbenzaldehyde (1.41 g, 4.58 mmol), anhydrous CuCl2 (1.84 g, 13.74 mmol) were combined in anhydrous ethanol (100 mL) and heated at reflux for 7 hours. The mixture was concentrated, diluted with ethyl acetate (300 mL), washed with water (100 mL) and then brine (150 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography on silica gel, eluting with 50% ethyl acetate/hexanes to 100% ethyl acetate, afforded the title compound in 55% yield, as a white solid. 1H-NMR (300 MHz, DMSO-6): δ 8.18 (d, J=7.5 Hz, 1H), 7.86-7.92 (m, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.55-7.60 (m, 1H), 7.15-7.17 (m, 4H), 6.96 (s, 2H), 4.84 (t, J=5.3 Hz, 1H), 3.62-3.36 (m, 4H), 2.48-2.50 (m, 1H), 2.06 (s, 6H), 1.67-1.78 (m, 5H), 1.32-1.39 (m, 5H). MS (ESI) m/z: 469 (M+H)+.

Provenance & Evidence