Acetic Acid → HCID 14233887, compound

Participants

Reaction Steps

A solution of 1,2,3,9-tetrahydro-3-[hydroxy[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-9-methyl-4H-carbazol-4-one (2.70 g) in glacial acetic acid (100 ml) was treated with p-toluenesulphonic acid monohydrate (10.80 g) and the stirred solution heated at reflux for 4 h. The cool, dark liquid was evaporated, treated with aqueous saturated sodium bicarbonate (250 ml) and extracted into ethyl acetate (4×250 ml). the combined, dried organic extracts were evaporated, and purified by SPCC. Elution with System A (978:20:2→945:50:5) afforded the free base of the title compound as a light yellow-brown solid (488 mg). A hot solution of the free base (87 mg) in ethanol (ca. 16 ml) was treated with a hot solution of maleic acid (38 mg) in ethanol (1 ml), and on cooling the precipitate was collected to give the title compound (81 mg), m.p. 205°-209°.

Provenance & Evidence