Sodium hydride → HCID 22727141, compound

HRID 2086245Notes

Reaction equation

HRID 2086245 reaction equation
[CH3:1][CH:2]1[NH:7][C:6](=[O:8])[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[H-].[Na+].C1(P(C2C=CC=CC=2)(O[NH2:27])=O)C=CC=CC=1>CN(C=O)C>[NH2:27][N:7]1[C:6](=[O:8])[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:3][CH:2]1[CH3:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 227270321-Piperazinecarboxylic acid, 3-methyl-5-oxo-, 1,1-dimethylethyl ester

Product 1

HCID 22727141HCID 22727141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 3-methyl-5-oxo-1-piperazinecarboxylate (1.1 g) was dissolved in DMF (20 ml) and treated with sodium hydride (0.25 g, in oil) with cooling on ice. After stirring at 50° C. for 1 hour, O-diphenylphosphinyl hydroxylamine (1.3 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 tert-butyl 4-amino-3-methyl-5-oxo-1-piperazinecarboxylate as a yellow 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-949b143a25dd4de0a691795ea3f75acd
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

Loading…