HCID 70873515, compound → HCID 70873482, compound

HRID 2172195Notes

Reaction equation

HRID 2172195 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)([OH:21])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:16][CH2:17][C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=3)([OH:21])[CH2:19][CH2:20]2)=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 70873515HCID 70873515, compound

Product 1

HCID 70873482HCID 70873482, compoundYield 90.6%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Benzyloxyphenyl)-4-(4-trifluoromethylphenyl)piperidin-4-ol (2 g) was dissolved in ethanol (20 ml) and ethyl acetate (20 ml). 20% palladium hydroxide on carbon (0.2 g) was added to the mixture and stirred at room temperature under a hydrogen atmosphere for 1.5 hours. The mixture was filtered through Celite to remove the catalyst, and the filtrate was concentrated under reduced pressure. The residue was washed with an ether-hexane mixed solvent to afford the title compound as a pale pink powder (1.43 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washThe residue was washed with an ether-hexane mixed solvent

Sources & evidence

ORD record
ord-bc976f3a68324ba7b071e21b1a3aea1a
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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