Ethyl Acetate → Benzyl 3-oxopiperazine-1-carboxylate

HRID 2186122Notes

Reaction equation

HRID 2186122 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].[C:8](Cl)(=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O>[CH2:10]([O:9][C:8]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 231360Piperazin-2-one

Product 1

HCID 736777Benzyl 3-oxopiperazine-1-carboxylateYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-piperazinone (10 g), benzyl chlorocarbonate (20.5 g), sodium carbonate (31.8 g), ethyl acetate (200 ml) and water (200 ml) was stirred at room temperature for 2 hours. The organic layer was separated, washed with saturated brine, dried (MgSO4) and concentrated. The resulting crystals was filtered, washed with ethyl acetate-ether and dried to give colorless crystals of the title compound (18.5 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe resulting crystals was filtered
  6. washwashed with ethyl acetate-ether
  7. customdried

Sources & evidence

ORD record
ord-b327c963bcaa408cafe0242430676a45
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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