Acetic Anhydride → 4-Acetyl-2-piperazinone

HRID 2109831Notes

Reaction equation

HRID 2109831 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C(N(CC)C(C)C)(C)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 231360Piperazin-2-one

Product 1

HCID 127445174-Acetyl-2-piperazinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of piperazin-2-one (2.50 g, 24.9 mmol) and N,N-diisopropylethylamine (4.78 mL, 27.5 mmol) in methylene chloride (50 mL) under an atmosphere of nitrogen, acetic anhydride (2.47 mL, 26.2 mmol) was added and stirred at the temperature for overnight. The resultant solution was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 90:10:1 mixture of chloroform, methanol, and ammonium hydroxide. Collection and concentration of appropriate fractions provided the title product.

Workup

  1. concentrationThe resultant solution was concentrated under vacuum
  2. additionThe residue was subjected to column chromatography on silica gel eluting with a 90:10:1 mixture of chloroform, methanol, and ammonium hydroxide
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-5ff3816b257e4a5390da37e27815c4de
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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