Trifluoroacetic acid → 4-Phenoxypiperidine

HRID 2223700Notes

Reaction equation

HRID 2223700 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>CO.[Pd]>[O:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12999576HCID 12999576, compound

Product 1

HCID 188784-Phenoxypiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-4-phenoxy-piperidine (420 mg, 1.6 mmol), Pd—C 10% (10 mg) and TFA (0.18 mL, 1,6 mmol) in MeOH (5 mL) is hydrogenated at room temperature and atmospheric pressure for 20 h. The mixture is filtered over Celite and the filtrate is concentrated under reduced pressure. The residue is dissolved in CH2Cl2, washed with sat. NaHCO3, filtered and concentrated to provide the title compound.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe mixture is filtered over Celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in CH2Cl2
  5. washwashed with sat. NaHCO3
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e9219d68e408401cbe1b1bf40f52c247
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

Loading…