Sodium Carbonate → Benzyl 3-oxopiperazine-1-carboxylate

HRID 2282243Notes

Reaction equation

HRID 2282243 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>CCOC(C)=O.O>[CH2:18]([O:17][C:15]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

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

Product 1

HCID 736777Benzyl 3-oxopiperazine-1-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of piperazine-2-one (2.00 g, 20.0 mmol) in EtOAc (50 mL) and water (50 mL), were added sodium carbonate (6.36 g, 60.0 mmol) and 95% benzyl chloroformate (3.59 mL, 24.0 mmol) and the mixture was stirred for 3 days at rt. To the mixture were added EtOAc (50 mL) and water (20 mL) and then organic layer was separated. The aqueous layer was extracted with EtOAc (30 mL×2). The combined organic layer was washed with brine (20 mL) and then dried over anhydrous sodium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was washed with diethyl ether (50 mL) to give title compound (3.98 g, 85%) as a colorless solid.

Workup

  1. customorganic layer was separated
  2. extractionThe aqueous layer was extracted with EtOAc (30 mL×2)
  3. washThe combined organic layer was washed with brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customInsoluble materials were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washThe residue was washed with diethyl ether (50 mL)

Sources & evidence

ORD record
ord-a2ace0e59d8a461eb57e9661f277467a
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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