Morpholine → HCID 18960596, compound

Participants

Reaction Steps

A solution of 4-bromo-3-methylbenzoic acid (5.00 g) in dry THF (60 ml) was added dropwise at -5° to +5° to 1,1'-carbonylbis[1H-imidazole](4.90 g) and stirred under nitrogen over 10 min. Stirring was continued at +23° for 4 h, and morpholine (6.1 ml) added dropwise over 1 min. After 16 h the solution was evaporated, treated with aqueous 2M hydrochloric acid (80 ml), and extracted with ethyl acetate (4×75 ml). The combined, dried organic extracts were washed with aqueous saturated sodium bicarbonate (100 ml), dried and evaporated. A solution of the residual oil in dichloromethane (60 ml) was adsorbed onto silica gel (Merck 7734) and the mixture applied as a plug to a flash column of silica gel (Merck 9385). Gradient elution with ethyl acetate:hexane (3:7→6:4) afforded the title compound as a cream solid (5.75 g).

Provenance & Evidence