Trifluoroacetic acid methylene chloride → tert-Butyl 4-(2-aminophenyl)piperidine-1-carboxylate

HRID 1419570Notes

Reaction equation

HRID 1419570 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](N(C2C=CC=CC=2)C(=O)OC(C)(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:29](F)(F)[C:30](O)=O.ClCCl>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:30]2[CH:29]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:8])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 54392086t-Butyl (1-t-Butoxycarbonylpiperidin-4-yl)phenylcarbamate

Product 1

HCID 22266191tert-Butyl 4-(2-aminophenyl)piperidine-1-carboxylate

Procedure

t-Butyl (1-t-butoxycarbonylpiperidin-4-yl)phenylcarbamate (290 mg) was dissolved in trifluoroacetic acid-dichloromethane (10%, 20 mL) and stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure and the residue was partitioned between aqueous sodium hydroxide (2M) and ether (30 mL). The organic layer was separated, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and cooled in ice. Di-t-butyldicarbonate (161 mg) was added and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure and the residue was purified by MPLC on silica gel, eluting with EtOAc/Hexane (5:95) to give the title compound as a clear oil (141 mg), δH (CDCl3) 1.55 (9H, s), 1.59 (2H, m), 1.82 (2H, m), 2.58 (1H, m), 2.77 (1H, m), 3.64 (2H, br s), 4.16 (2H, m), 6.68-6.79 (2H, m), 7.01-7.26 (2H, m).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between aqueous sodium hydroxide (2M) and ether (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  7. temperaturecooled in ice
  8. additionDi-t-butyldicarbonate (161 mg) was added
  9. stirringthe mixture was stirred at room temperature for 30 min
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by MPLC on silica gel
  12. washeluting with EtOAc/Hexane (5:95)

Sources & evidence

ORD record
ord-440995c7154948ddb8398d636b6b85b8
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

Loading…