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

HRID 1039607Notes

Reaction equation

HRID 1039607 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 190%

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 50 atms of atmosphere of hydrogen at 24-26° C. for 7 hr 40 min. The reaction mixture was filtered to remove the catalyst followed by concentration in vacuo to give 3.89 g of colorless 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 772 mg (37.7% 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-346ff289d54443c29d51b4cfa2d55ed1
Source dataset
uspto-grants-2013_10
Patent number
US08552188B2

Reaction notes

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