Water → 3-[4-(4-Fluorophenoxy)benzyloxy]piperidine

HRID 602186Notes

Reaction equation

HRID 602186 reaction equation
[OH-].[K+].FC(F)(F)C([N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[CH2:8]1)=O.O>CO>[F:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][C:18]2[CH:17]=[CH:16][C:15]([CH2:14][O:13][CH:9]3[CH2:10][CH2:11][CH2:12][NH:7][CH2:8]3)=[CH:20][CH:19]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 589925921-Trifluoroacetyl-3-[4-(4-fluorophenoxy)benzyloxy]piperidine

Product 1

HCID 589926953-[4-(4-Fluorophenoxy)benzyloxy]piperidineYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 mol/L aqueous potassium hydroxide solution (2 mL) was added to 1-trifluoroacetyl-3-[4-(4-fluorophenoxy)benzyloxy]piperidine (434 mg, 1.09 mmol) in methanol (4 mL). The mixture was refluxed for 2 hours and was allowed to cool. Water was then added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and the washed product was dried over magnesium sulfate. The solvent was evaporated to give 314 mg (95%) of the desired compound as a colorless oil.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureto cool
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialthe washed product was dried over magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-595462e0dfde48798d401963a45daa78
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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