1-Benzyloxycarbonyl-4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine → 4-[4-(Trifluoromethyl)phenyl]piperidin-4-ol

HRID 1458787Notes

Reaction equation

HRID 1458787 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C:14]([OH:27])([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:27][C:14]1([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=2)[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 220976691-Benzyloxycarbonyl-4-hydroxy-4-(4-trifluoromethylphenyl)-piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 152926054-[4-(Trifluoromethyl)phenyl]piperidin-4-olYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyloxycarbonyl-4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine (12.3 g, 32.4 mmol), ethanol (150 mL), and 10% palladium on carbon (1.4 g) was hydrogenated in a Parr apparatus (initial hydrogen pressure was 48 psi). After 2.5 hours, the mixture was filtered through celite and concentrated. The residue was triturated with ether/hexane to obtain 4.98 g (63%) of 4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine as a white solid which had mp 130.5°-132° C. Analysis calculated for C12 H14F3NO--0.25 H2O: C, 57.71; H, 5.85; N, 5.61. Found: C, 57.91; H 5.77; N, 5.54.

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationconcentrated
  3. customThe residue was triturated with ether/hexane

Sources & evidence

ORD record
ord-4862156636c44d8f8cf9e449d1fa9648
Source dataset
uspto-grants-1998_12
Patent number
US05852040

Reaction notes

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