Sodium hydride → Benzyl 4-amino-3-oxopiperazine-1-carboxylate

HRID 2086229Notes

Reaction equation

HRID 2086229 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C1(P(C2C=CC=CC=2)(O[NH2:29])=O)C=CC=CC=1>CN(C=O)C>[NH2:29][N:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12][C:13]1=[O:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 10955453O-(Diphenylphosphinyl)hydroxylamine

Product 1

HCID 22727156Benzyl 4-amino-3-oxopiperazine-1-carboxylateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(Benzyloxycarbonyl)-2-piperazinone (4.685 g) was dissolved in DMF (170 ml) and combined with sodium hydride (800 mg, in oil) with cooling on ice. After stirring at room temperature for 30 minutes, O-diphenylphosphinyl hydroxylamine (4.896 g) was added and the mixture was stirred at 50° C. for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was combined with aqueous sodium bicarbonate and extracted with dichloromethane. The extract was dried and concentrated to obtain the title compound 1-amino-4-benzyloxycarbonyl-2-piperazinone (4.8 g) as a colorless oil.

Workup

  1. temperaturewith cooling on ice
  2. stirringthe mixture was stirred at 50° C. for 15 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with dichloromethane
  5. customThe extract was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-328225b4edb24604a071d2160f817db0
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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