Trifluoroacetic acid → HCID 57365150, compound

HRID 715556Notes

Reaction equation

HRID 715556 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([NH2:14])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118048098HCID 118048098, compound

Product 1

HCID 57365150HCID 57365150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-(4-bromophenyl)piperidin-4-ylcarbamate (365 mg) is dissolved in dichloromethane (10 mL), treated with trifluoroacetic acid (780 μL) and stirred for 6 hours at room temperature. Then the mixture is partitioned between dichloromethane and saturated aqueous K2CO3 solution and stirred vigorously for 30 minutes. The phases are separated and the organic phase is washed with saturated aqueous K2CO3 solution. The organic phase is dried (MgSO4) and concentrated to give the title compound. LC (method 2): tR=0.93 min; Mass spectrum (ESI+): m/z=255 [M+H]+.

Workup

  1. customThen the mixture is partitioned between dichloromethane and saturated aqueous K2CO3 solution
  2. stirringstirred vigorously for 30 minutes
  3. customThe phases are separated
  4. washthe organic phase is washed with saturated aqueous K2CO3 solution
  5. dry with materialThe organic phase is dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec1cf59ac9fa4de19f402cfc5c36cb67
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

Loading…