tert-Butyl 4-((2-(trifluoromethyl)phenyl)amino)piperidine-1-carboxylate → Piperidin-4-yl-(2-trifluoromethylphenyl)amine

HRID 552129Notes

Reaction equation

HRID 552129 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:22])([F:23])[F:24])[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 66591750tert-Butyl 4-((2-(trifluoromethyl)phenyl)amino)piperidine-1-carboxylate

Product 1

HCID 54902682Piperidin-4-yl-(2-trifluoromethylphenyl)amineYield 99.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(2-trifluoromethylphenylamino)piperidine-1-carboxylic acid tert-butyl ester (0.87 g, 2.52 mmol) in dichloromethane and trifluoroacetic acid (18 mL, 2:1) was stirred at ambient temperature overnight, the solvents were removed by evaporation. The residue was dissolved in ethyl acetate, and the resulting solution was washed with aqueous saturated NaHCO3 and brine, dried over anhydrous Na2SO4 and concentrated to give piperidin-4-yl-(2-trifluoromethylphenyl)amine (0.612 g, 99%) which was used directly for next step reaction without further purification. MS (ES+) m/z 245.0 (M+1).

Workup

  1. customthe solvents were removed by evaporation
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe resulting solution was washed with aqueous saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-44bf684b51304b46bea8dd1d5d60d737
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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