1,2-Dimethoxyethane → HCID 70090434, compound

Participants

Reaction Steps

Sodium hydride (73% dispersion in oil; 20 mg) was added to a stirred solution of 3,4-dihydrobenzofuro[3,2-c]pyridin-1(2H)-one (95 mg) in dry dimethoxyethane (3 ml) under nitrogen. After 30 min. 4-(chloromethyl)-5-methyl-1-(triphenylmethyl)-1H-imidazole (227 mg) was added and the mixture was stirred at 50° for 18h. Acetic acid (1 ml) and water (1 ml) were added and the solution was heated at reflux for 1h. The mixture was poured into 8% sodium bicarbonate solution (30 ml) and extracted with dichloromethane (3×15 ml). The combined, dried organic extracts were evaporated to give a solid (ca.420 mg) which was purified by SPCC eluting with System A (200:10:1) to give the free base of the title compound (77 mg). This was dissolved in absolute ethanol (2 ml) and treated with a solution of maleic acid (33 mg) in absolute ethanol (1 ml). The solvent was removed in vacuo and the residue was triturated with dry ether (3×5 ml) to give the title compound (85mg), m.p. 285°-286°, t.l.c. (System A, 200:10:1) Rf 0.24.

Provenance & Evidence