Trifluoroacetic acid → 4-(2-Methoxyphenyl)piperidine

HRID 2223704Notes

Reaction equation

HRID 2223704 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22629567Tert-butyl 4-(2-methoxyphenyl)piperidine-1-carboxylate

Product 1

HCID 5447384-(2-Methoxyphenyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (190 mg, 0.65 mmol), and TFA (0.35 mL, 4.8 mmol) in dry CH2Cl2 (5 mL) is stirred at room temperature under nitrogen for 2 h. The mixture is concentrated under reduced pressure, and the residue is combined with CH2Cl2/sat. aqueous NaHCO3. The aqueous layer is extracted twice with CH2Cl2, the combined organic extracts are washed with brine, dried (MgSO4), filtered and concentrated to provide the title compound.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. extractionThe aqueous layer is extracted twice with CH2Cl2
  3. washthe combined organic extracts are washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0104fe3a063c4bbea9d7e3d4edeefeb0
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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