Sodium Iodide → HCID 9828743, compound

Participants

Reaction Steps

To a stirred solution of 1-(5-bromopent-1-yl)-5-(3,4-difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone (0.357 g, 0.88 mmol) in dioxane (10 mL) was added 4-methoxycarbonyl-4-phenylpiperidine (0.388 g, 1.77 mmol), potassium carbonate (0.544 g, 2.65 mmol) and sodium iodide (0. g, 1.77 mmol), and the mixture refluxed for 24 hours. The reaction mixture was cooled to room temperature, concentrated and partitioned between chloroform (40 mL) and water (5 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (ethyl acetate: methanol, 4.4:0.6) to yield 0.235 g (48%) of the required product as a colorless oil. Hydrochloride salt (recrystallized from ether) : white solid; m.p. 180-182° C. Analysis calculated for C29H34ClF2N3O5.1.7 H2O: C, 57.23; H,6.19. Found: C, 57.14; H, 6.20.

Provenance & Evidence