2,5-Piperazinedione → 1,4-Diacetyl-2,5-piperazinedione

HRID 887970Notes

Reaction equation

HRID 887970 reaction equation
[NH:1]1[CH2:6][C:5](=[O:7])[NH:4][CH2:3][C:2]1=[O:8].[C:9]([O-:12])(=O)[CH3:10].[Na+].[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([N:1]1[CH2:6][C:5](=[O:7])[N:4]([C:9](=[O:12])[CH3:10])[CH2:3][C:2]1=[O:8])(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 78172,5-PiperazinedioneHCID 7918Acetic AnhydrideHCID 517045Sodium Acetate

Product 1

HCID 5403711,4-Diacetyl-2,5-piperazinedioneYield 61%

Conditions

Temperature
110 °C

Procedure

25.0 g of global 2,5-piperazinedione 1 [2,5-piperazinedione (Aldrich G640-6), 25.0 g, 0.218 mol] in 100 mL of acetic anhydride (Ac2O) was mixed with sodium acetate (NaOAc) (17.96 g, 0.0218 mol). The mixture was heated at 110° C. for 8 h using a double coiled condenser under an Ar atmosphere. After Ac2O was removed by evaporation, the residue was dissolved in AcOEt, washed with 10% citric acid, 10% NaHCO3 and saturated NaCl (three times each), dried over Na2SO4, and concentrated in vacuo. The residue was triturated with ether to form a solid. This solid was recrystallized from EtOAc with ether-hexane to afford 26.4 g (61%) of N,N′-diacetyl-2,5-piperazinedione 1.

Workup

  1. customAfter Ac2O was removed by evaporation
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with 10% citric acid, 10% NaHCO3 and saturated NaCl (three times each),
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ether
  7. customto form a solid
  8. customThis solid was recrystallized from EtOAc with ether-hexane

Sources & evidence

ORD record
ord-12ee03829d334d08a0a25d322ed8fe8e
Source dataset
uspto-grants-2012_08
Patent number
US08247552B2

Reaction notes

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