1-Benzyl-4-(p-trifluoromethylphenoxy)piperidine → 4-(4-(Trifluoromethyl)phenoxy)piperidine

HRID 437575Notes

Reaction equation

HRID 437575 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[F:24][C:21]([F:22])([F:23])[C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 129995801-Benzyl-4-(p-trifluoromethylphenoxy)piperidineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 36883924-(4-(Trifluoromethyl)phenoxy)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 46.0 g of 1-benzyl-4-(p-trifluoromethylphenoxy)piperidine, the free base of Part (a), in 250 ml. of 95% ethanol is treated with 6.0 g of 10% palladium-on-charcoal catalyst and is shaken with hydrogen gas at 50° C. until the theoretical amount of hydrogen is absorbed. The suspension is cooled, filtered, and the solvent is removed. The residual oil is fractionally distilled under reduced pressure and the fraction which boils at 74°-76° C/0.05 mm is collected. The collected oil crystallizes on standing to give a solid of 4-(p-trifluoromethylphenoxy)piperidine.

Workup

  1. customis absorbed
  2. temperatureThe suspension is cooled
  3. filtrationfiltered
  4. customthe solvent is removed
  5. distillationThe residual oil is fractionally distilled under reduced pressure
  6. customthe fraction which boils at 74°-76° C/0.05 mm is collected
  7. customThe collected oil crystallizes

Sources & evidence

ORD record
ord-4ede845a94284a8cbb7621fc786f6722
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

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