1,4-Dioxane hydrochloride → HCID 178462017, compound

Participants

Reaction Steps

To 205 mg of tert-butyl ({1-[2,6-difluoro-4-(1H-tetrazole-5-yl)phenyl]-3-phenylpiperidin-4-yl}methyl)[(1R)-1-(1-naphthyl)ethyl]carbamate was added 2.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was then added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 158 mg of (1R)—N-({1-[2,6-difluoro-4-(1H-tetrazol-5-yl)phenyl]-3-phenylpiperidin-4-yl}methyl)-1-(1-naphthyl)ethaneamine. 2.0 mL of hydrogen chloride/1,4-dioxane solution was added thereto, followed by concentration under reduced pressure, and to the obtained residue was then added about 3 mL of isopropanol, followed by heating. The mixture was left to be cooled to room temperature, and the precipitate was collected by filtration, and dried under reduced pressure to obtain 153 mg of (1R)—N-({1-[2,6-difluoro-4-(1H-tetrazol-5-yl)phenyl]-3-phenylpiperidin-4-yl}methyl)-1-(1-naphthyl)ethaneamine hydrochloride as a white solid.

Provenance & Evidence