Diethyl Oxalate → 1-Ethyl-2,3-piperazinedione

HRID 371686

Reaction equation

HRID 371686 reaction equation
CCO[C:4]([C:6]([O:8]CC)=O)=[O:5].[CH2:11]([NH:13][CH2:14][CH2:15][NH2:16])[CH3:12]>C(O)C>[CH2:11]([N:13]1[CH2:14][CH2:15][NH:16][C:6](=[O:8])[C:4]1=[O:5])[CH3:12]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 66071N-Ethylethylenediamine

Product 1

HCID 1088121-Ethyl-2,3-piperazinedioneYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a mixture comprising 8 g of a diethyl ester of oxalic acid and 8 ml of ethanol was dropped at room temperature 4.4 g of N-ethyl ethylenediamine. The resulting mixture was allowed to react for 3 hours, and then heated to remove the ethanol. Subsequently, the residue was recrystallized from 10 ml of dioxane to obtain 5.4 g of 1-ethyl-2,3-dioxo-piperazine, m.p. 124° C, yield 76.0%.

Workup

  1. customto react for 3 hours
  2. temperatureheated
  3. customto remove the ethanol
  4. customSubsequently, the residue was recrystallized from 10 ml of dioxane

Sources & evidence

ORD record
ord-933aa54376704b39bf9a3efd64b9693c
Source dataset
uspto-grants-1978_05
Patent number
US04087424

Linked notes

Loading…