Piperazin-2-one → 2-(3-Oxopiperazin-1-yl)-2-iminoethylchloride hydrochloride

HRID 622430Notes

Reaction equation

HRID 622430 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Cl.[Cl:9][CH2:10][C:11](=[NH:14])OC>CO>[ClH:9].[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][N:6]([C:11](=[NH:14])[CH2:10][Cl:9])[CH2:7]1

Participants

4

Reactant 2

HCID 231360Piperazin-2-oneHCID 12680765Methyl 2-chloroethanimidate--hydrogen chloride (1/1)

Product 1

HCID 212929452-(3-Oxopiperazin-1-yl)-2-iminoethylchloride hydrochlorideYield 197.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.64 g of 2-oxopiperazine were added to a solution of 12.4 g of methyl 2-chloroacetimidate hydrochloride in 44.8 ml of anhydrous methanol, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, a small amount of insoluble material was filtered off and the solvent was distilled off from the filtrate. Ether was added to the residue, and the precipitated crystals were collected by filtration and washed with ether, giving 18.0 g of 2-(3-oxopiperazin-1-yl)-2-iminoethylchloride hydrochloride.

Workup

  1. customAfter completion of the reaction
  2. filtrationa small amount of insoluble material was filtered off
  3. distillationthe solvent was distilled off from the filtrate
  4. additionEther was added to the residue
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-0db605532b0b42ad8279c68bb28ca130
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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