1-[4-(Phenylmethoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine → SS-3227

HRID 1039610Notes

Reaction equation

HRID 1039610 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:16][CH2:17][CH:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:30])[F:31])=[CH:24][CH:23]=3)[CH2:19][CH2:20]2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 684830771-[4-(Phenylmethoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 11653258SS-3227Yield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

After 1-(4-Benzyloxyphenyl)-4-[4-(Trifluoromethoxy)phenoxy]piperidine (20.0 g) and ethyl alcohol (200 mL) was mixed and then (50% wet) 5 w/w % palladium on carbon (1 g) was added. The resulting mixture was stirred under 4 atms of atmosphere of hydrogen at 60-61° C. for 3 hr. The reaction mixture was then cooled to room temperature and was filtered to remove the catalyst followed by concentration in vacuo to give 16.2 g (99.5% yield) of an ivory crystal target compound.

Workup

  1. filtrationwas filtered
  2. customto remove the catalyst
  3. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-0ed097960f6e4ee4ac67f0e46c50d713
Source dataset
uspto-grants-2013_10
Patent number
US08552188B2

Reaction notes

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