Diethyl Oxalate → 2,3-Piperazinedione, 1-butyl-

HRID 1099209Notes

Reaction equation

HRID 1099209 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][NH2:8])[CH2:2][CH2:3][CH3:4].C(O[C:12](=[O:18])[C:13]([O:15]CC)=O)C>C(O)(C)C>[CH2:1]([N:5]1[CH2:6][CH2:7][NH:8][C:12](=[O:18])[C:13]1=[O:15])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 519668n-Butylethylenediamine

Product 1

HCID 2006272,3-Piperazinedione, 1-butyl-Yield 44%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of N-butylethylenediamine (4.78 ml, 34.4 mmol) in isopropanol (60 ml) at 0° C. under a nitrogen atmosphere was added diethyloxalate (4.67 ml, 34.4 mmol). The reaction was allowed to warm to rt and heated to reflux for 6 h. The reaction was concentrated in vacuo and purified via flash chromatography (silica) to yield 1-butylpiperazine-2,3-dione (44%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 h
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified via flash chromatography (silica)

Sources & evidence

ORD record
ord-85d6b20a58504fa4b3050b5da4ae8cd4
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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