Ethylenediamine → Piperazine,2-(3-methoxy-4-nitrophenyl)-

HRID 344868Notes

Reaction equation

HRID 344868 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([CH:14]=O)=O)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH2:16]([NH2:19])[CH2:17][NH2:18]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]2[CH2:14][NH:19][CH2:16][CH2:17][NH:18]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 543850723-Methoxy-4-nitrophenylglyoxal

Product 1

HCID 54315606Piperazine,2-(3-methoxy-4-nitrophenyl)-

Procedure

(RS)-2-(3-Methoxy-4-nitrophenyl)piperazine was prepared according to the method described in Patent Application FR 2,351,108, but starting with 3-methoxy-4-nitrophenylglyoxal (36 g) and ethylenediamine (12.1 g). The crude product is purified by chromatography on 230-400 mesh silica (800 g) suspended in a mixture of dichloromethane (70%), ethanol (26%) and triethylamine (4%) and elution with the same mixture (2 liters). After concentration of the eluate under reduced pressure (20 kPa) at approximately 50° C., the expected product (18 g) is obtained in the form of a red oil, which was used without further purification for the subsequent steps.

Workup

  1. customThe crude product is purified by chromatography on 230-400 mesh silica (800 g)
  2. additionsuspended in a mixture of dichloromethane (70%), ethanol (26%) and triethylamine (4%) and elution with the same mixture (2 liters)

Sources & evidence

ORD record
ord-d1df5075bf8744c4bb83fe2b7fdb88c4
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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