Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-[4-(4-Trifluoromethylphenoxy)piperidin-1-yl]ethanol

A mixture of 1-[2-(tetrahydropyran-2-yloxy)ethyl]-4-(4-trifluoromethylphenoxy)piperidine (1.69 g, 4.53 mmol) prepared in Reference Example 13 and pyridinium p-toluenesulfonate (114 mg, 0.45 mmol) in ethanol (50 ml) was stirred at 60 to 70° C. for 6 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, 10% sodium hydroxide aqueous solution was added, and the mixture was extracted with methylene chloride. The extract was washed with brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford 2-[4-(4-trifluoromethylphenoxy)piperidin-1-yl]ethanol (1.19 g, yield 91%) as a colorless oil.

1. customto return to room temperature
2. concentrationconcentrated under reduced pressure
3. additionTo the residue, 10% sodium hydroxide aqueous solution was added
4. extractionthe mixture was extracted with methylene chloride
5. washThe extract was washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

ORD record

ord-2b669756d0854291883ab4c9edd3c42b

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2