Hydrochloric Acid → 4-({[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}oxy)benzoic acid

To 232 mg of 4-(methoxycarbonyl)phenyl 3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidine-1-carboxylate were added 6.0 mL of THF, 3.0 mL of methanol, and 3.0 mL of a 1 M aqueous sodium hydroxide solution, followed by stirring at room temperature overnight. After neutralizing by addition of 3.0 mL of 1 M hydrochloric acid, the reaction mixture was concentrated under reduced pressure. To the residue was added water, followed by extraction with chloroform, and 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). This was dissolved in a small amount of chloroform, and hexane was added thereto. Then, the precipitate was isolated by filtration, and dried under reduced pressure at 50° C. to obtain 66 mg of 4-({[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}oxy)benzoic acid as a white solid.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionTo the residue was added water
3. extractionfollowed by extraction with chloroform
4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
5. filtrationAfter filtration
6. concentrationthe filtrate was concentrated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (chloroform-methanol)
8. dissolutionThis was dissolved in a small amount of chloroform, and hexane
9. additionwas added
10. customThen, the precipitate was isolated by filtration
11. customdried under reduced pressure at 50° C.

ORDレコード

ord-5d2daa4dea384e89ae30112166bebf47

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08153658B2