Diethyl Oxalate → 1,4-Dimethylpiperazine-2,3-dione

HRID 1176955Notes

Reaction equation

HRID 1176955 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].[C:7]([O:14]CC)(=O)[C:8]([O:10]CC)=O>C(OCC)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH3:6])[C:7](=[O:14])[C:8]1=[O:10]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 8070N,N'-Dimethylethylenediamine

Product 1

HCID 3229831,4-Dimethylpiperazine-2,3-dioneYield 97.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of N,N′-dimethylethylenediamine (25.0 g, 0.28 mol) in 150 mL of dry diethyl ether was added diethyl oxalate (38.5 mL, 0.28 mol) in one portion. After a few minutes white crystals started to precipitate. The reaction mixture was stirred at room temperature overnight. The product was filtered and washed with dry diethyl ether. The product was dried under vacuum at 47° C. overnight to give colorless crystals (38.64 g, 96%). 1H NMR (200 MHz, CDCl3, δ): 3.50 (s, 4H), 2.99 (s, 6H). 13C{1H} NMR (200 MHz, CDCl3, δ): 157.35, 45.91, 34.74.

Workup

  1. waitAfter a few minutes white crystals started
  2. customto precipitate
  3. filtrationThe product was filtered
  4. washwashed with dry diethyl ether
  5. customThe product was dried under vacuum at 47° C. overnight

Sources & evidence

ORD record
ord-f06fbbf112634931a5812a1a3f816a0f
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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