1,4-Dioxane hydrochloride → 3,5-difluoro-4-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoic acid hydrochloride

Participants

Reaction Steps

To 230 mg of 4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-3,5-difluorobenzoic acid was added 1.5 mL of a 4 M hydrogen chloride/1,4-dioxane solution at room temperature. After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was solidified by isopropanol and diisopropyl ether, and then collected by filtration. The obtained solid was purified by silica gel column chromatography (methanol-chloroform), and a 4 M hydrogen chloride/1,4-dioxane solution was then added thereto. The mixture was concentrated under reduced pressure, and the obtained individual product was washed with isopropanol to obtain 140 mg of 3,5-difluoro-4-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoic acid hydrochloride.

Provenance & Evidence