Trifluoroacetic acid → Benzyl 2-phenylpiperazine-1-carboxylate

HRID 473817Notes

Reaction equation

HRID 473817 reaction equation
[C:1]1([CH:7]2[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9][N:8]2[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][N:8]2[C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 675145701-Benzyl 4-tert-butyl 2-phenylpiperazine-1,4-dicarboxylate

Product 1

HCID 16740571Benzyl 2-phenylpiperazine-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To 1-benzyl 4-tert-butyl 2-phenylpiperazine-1,4-dicarboxylate (0.84 g, 2.12 mmol) in dichloromethane (5.0 mL) added drop wise trifluoroacetic acid (5.0 mL) and maintained at 25° C. for 90 minutes. The reaction mixture was concentrated, and the residue dissolved in ethyl acetate (60 mL). The solution was washed with saturated aqueous sodium carbonate (30 mL) and brine (20 mL), and then dried over anhydrous sodium sulfate, filtered and concentrated to yield benzyl 2-phenylpiperazine-1-carboxylate (0.59 g, 94% yield). MS (EI) for C18H20N2O2: 297 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate (60 mL)
  3. washThe solution was washed with saturated aqueous sodium carbonate (30 mL) and brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-08fe7b18c6e1455295f2ab95a09a6593
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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