Hydrochloric Acid → 1-[4-(Trifluoromethoxy)phenyl]piperidin-4-ol

HRID 856026Notes

Reaction equation

HRID 856026 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:20])([F:19])[O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.Cl>CO>[F:20][C:4]([F:3])([F:19])[O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:13][CH2:14][CH:15]([OH:18])[CH2:16][CH2:17]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 230815881-[4-(Trifluoromethoxy)phenyl]piperidin-4-one

Product 1

HCID 230815701-[4-(Trifluoromethoxy)phenyl]piperidin-4-olYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (324 mg, 8.56 mmol) was added to a solution of 1-(4-trifluoromethoxyphenyl) piperidin-4-one (1.11 g, 4.28 mmol) prepared in Reference Example 22 in methanol (30 ml) while cooling in an ice-bath, and the mixture was stirred for 30 minutes. To which 10% hydrochloric acid was added, and the resulting mixture was concentrated under reduced pressure. To the residue saturated sodium bicarbonate aqueous solution was added, and the mixture was extracted with methylene chloride. The extract was washed with water and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to afford 1-(4-trifluoromethoxyphenyl)piperidin-4-ol (1.08 g, yield 97%) as a white powder.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. additionTo the residue saturated sodium bicarbonate aqueous solution was added
  4. extractionthe mixture was extracted with methylene chloride
  5. washThe extract was washed with water and 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 (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-4070bf017c504f78b2ab31c14a247b12
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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