Morpholine → HCID 53892685, compound

Participants

Reaction Steps

To a solution of N-dodecyl-3-bromo-4-(2-bromoethoxy)-5-(m-trifluoromethylphenyl)-benzamide (0.294 g, 0.46 mmol, 1 eq) in CH3CN (4 mL) was added morpholine (0.50 mL, 0.57 mmol 1.24 eq) and K2CO3 (0.509 g, 3.68 mmol, 8 eq). The reaction was heated at reflux overnight. The solids were filtered off and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (50% EtOAc:hexane) to afford the title compound (0.296 g, 100%) as a colorless oil. 1H NMR (DMSO-d6) δ 8.53 (bt, 1H); 8.11 (d, 1H); 7.88-7.83 (m, 3H); 7.78 (d, 1H); 7.72 (dd, 1H); 3.63(dd, 2H); 3.40 (dd, 4H); 3.21 (dd, 2H); 2.38 (dd, 2H); 2.15 (dd, 4H); 1.48 (dd, 2H); 1.22 (m, 18H); 0.82 (t, 3H); IR (KBr) 3400, 2900, 2800, 1630, 1540, 1450, 1330, 1310, 1170, 1120, 700 cm−1; mass spectrum [(+)APCI], m/z 641/643 (M+H)+; Anal. Calcd. for C31H34BrF3N2O4: C, 59.90; H, 6.91; N, 4.37, Found: C, 58.58; H, 7.01; N, 4.18.

Provenance & Evidence