Ammonia → HCID 22671418, compound

Participants

Reaction Steps

The 1-[3-(4-diethylcarbamoylphenyl)-3-(3-methoxyphenyl)propyl]-4-(1,3-dihydro-2H-benzimidazol-2-on-1-yl)piperidine (1.196 g) obtained in Example 1 was dissolved in dichloromethane (24 ml), added with a solution of boron tribromide in dichloromethane (1.0 M, 8.8 ml) and stirred at room temperature for 2 hours. The reaction mixture was slowly added with methanol (6 ml) with ice cooling to quench the reaction and then added with 7.5 N aqueous ammonia (40 ml). The layers were separated, and the aqueous layer was extracted with dichloromethane (20 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (24 ml) and added with a solution of hydrochloric acid in methanol (8.8 ml), and then the solvent was evaporated under reduced pressure again. The residue was purified by LH-20 column chromatography (elution solvent: dichloromethane:methanol=1:1) to obtain 1.057 g of the title compound. Yield: 85%.

Provenance & Evidence