Red-Al → HCID 22380765, compound

Participants

Reaction Steps

The 1-[2-[2-(4-diethylcarbamoylbenzyl)phenoxy]ethyl]-4-(2-hydroxymethyl-1H-benzimidazol-1-yl)piperidine (64 mg) obtained in Example 84 was dissolved in tetrahydrofuran (1.3 ml), added with a solution of Red-Al in toluene (65%, 0.18 ml) and stirred at room temperature for 2.5 hours. After the reaction mixture was slowly poured into ice 10 g with ice cooling to quench the reaction and the layers were separated, the aqueous layer was extracted with dichloromethane (30 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: dichloromethane:methanol:aqueous ammonia=9:1:0.1) to obtain 31 mg of the title compound. Yield: 50%.

Provenance & Evidence