Trifluoroacetic acid → 1-Benzylpiperazin-2-one

HRID 1672153Notes

Reaction equation

HRID 1672153 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](=[O:28])[CH2:16]1)=O)(C)(C)C>ClCCl>[CH2:21]([N:18]1[CH2:19][CH2:20][NH:15][CH2:16][C:17]1=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10891590Tert-butyl 4-benzyl-3-oxopiperazine-1-carboxylate

Product 1

HCID 15143031-Benzylpiperazin-2-oneYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 35 mL of TFA in dichloromethane was added 4-benzyl-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (10.39 g, 35.8 mmol) in portions. After 18 hours the solution was concentrated via rotary evaporator and H20 was added. The pH was adjusted to 12 with 4M NaOH. The mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give 1-benzyl-piperazin-2-one (6.29 g, 92%) as an oil.

Workup

  1. concentrationAfter 18 hours the solution was concentrated via rotary evaporator and H20
  2. additionwas added
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff7696b883da4cfa8634c53f2e1e5d86
Source dataset
uspto-grants-2011_08
Patent number
US07998963B2

Reaction notes

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