Trifluoroacetic acid → 4-[(1-Methylpiperidin-4-yl)oxy]-3-(trifluoromethyl)aniline

HRID 1465011Notes

Reaction equation

HRID 1465011 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)OC(C)(C)C)=[CH:11][C:10]=2[C:23]([F:26])([F:25])[F:24])[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[C:23]([F:24])([F:25])[F:26])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67359882t-Butyl 4-(1-methylpiperidine-4-yloxy)-3-(trifluoromethyl)phenylcarbamate

Product 1

HCID 221810464-[(1-Methylpiperidin-4-yl)oxy]-3-(trifluoromethyl)anilineYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl 4-(1-methylpiperidine-4-yloxy)-3-(trifluoromethyl)phenylcarbamate (82 mg, 0.299 mmol) was dissolved in methylene chloride (1 mL), and TFA (1 mL) was added thereto. The reaction mixture was stirred at room temperature for 2 hours and then concentrated. The reaction mixture was diluted with ethylene chloride and washed with sat. NaHCO3 solution. The organic layer was dried with Na2SO4, filtered and concentrated to obtain the title compound (63 mg, 77%) without further purification.

Workup

  1. concentrationconcentrated
  2. additionThe reaction mixture was diluted with ethylene chloride
  3. washwashed with sat. NaHCO3 solution
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b264990339904e0395a6d42805a254d1
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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