4-[4-(Trifluoromethoxy)phenoxy]pyridine → 4-[4-(Trifluoromethoxy)phenoxy]piperidine

HRID 1799514Notes

Reaction equation

HRID 1799514 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[H][H]>C(O)(=O)C.[Pt](=O)=O>[F:18][C:2]([F:1])([F:17])[O:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 453809774-[4-(Trifluoromethoxy)phenoxy]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidineYield 162.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

After 4-[4-(Trifluoromethoxy)phenoxy]pyridine (2.00 g) was dissolved in acetic acid (20 mL) and platinum(IV) oxide (200 mg) was added. The resulting mixture was stirred under 4 atms of atmosphere of hydrogen at 23-30° C. for 12 hr. The reaction mixture was filtered to remove the catalyst followed by concentration in vacuo to give 3.32 g of yellow oily crude product. The crude product was dissolved in toluene (100 mL) and was washed three times with 10 w/v % NaOHaq (50 mL×3) and then was washed three times with water (50 mL×3). The organic layer was condensed under reduced pressure to give 675 mg (33.0% yield) of a pale yellow crystal target compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-99272bdca2964dd7b5bbaf474cd5841b
Source dataset
uspto-grants-2013_01
Patent number
US08344148B2

Reaction notes

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