Benzoyl chloride → HCID 4779138, compound

Participants

Reaction Steps

Cyclohexylmethylamine (4.37 mL, 33.6 mmol) was added to a solution of benzoyl chloride (2.47 mL, 21 mmol) in THF (20 mL) at 0° C., and stirring continued 16 h. The mixture was filtered, diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (10 mL), dried (Na2SO4), and concentrated in vacuo. The product crystallised (2.1 g, 45%) 1H-NMR (300 MHz, CDCl3) δH 7.76 (1H, m, Ar); 7.29 (8H, m, Ar); 1.04 (2H, m, CH2); 1.14 (2H, m, CH2); 1.61 (7H, m, 3×CH2); 3.23 (2H, t, J=6.78 Hz, N—CH2); 6.15 (1H, s, NH); 7.37 (3H, m, ArH), 7.70 (2H, m, ArH); LCMS (ESI+) 218 [M+H]+.

Provenance & Evidence