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

HRID 856019Notes

Reaction equation

HRID 856019 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:25][C:23]([F:24])([F:26])[C:20]1[CH:21]=[CH:22][C:17]([O:16][CH:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][OH:7])[CH2:15][CH2:14]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 230813391-[2-(Tetrahydropyran-2-yloxy)ethyl]-4-(4-trifluoromethylphenoxy)piperidine

Product 1

HCID 694816382-[4-(4-Trifluoromethylphenoxy)piperidin-1-yl]ethanolYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2b669756d0854291883ab4c9edd3c42b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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