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Piperazine → 2-Piperazino-4,5-dichloronitrobenzene

HRID 248797
Notes
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Reaction equation

HRID 248797 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:13]1([C:2]2[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4837PiperazineHCID 69832,4,5-TrichloronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 197621472-Piperazino-4,5-dichloronitrobenzeneYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

68 g (0.3 mol) of 2,4,5-Trichloronitrobenzene and 77.4 g (0.9 mol) of piperazine were stirred in 100 ml of a dimethylformamide in the presence of 31 g of anhydrous potassium carbonate for one hour at a room temperature of 25° C. to 40° C. and then for one hour at 70° to 80° C. to obtain 49.5 g of 2-piperazino-4,5-dichloronitrobenzene. This compound was reacted with 2-ethylhexanoyl chloride in a solvent of acetonitrile in the presence of pyridine to obtain 2-[N-(2-hexanoyl)piperazino]-4,5-dichloronitrobenzene.

Sources & evidence

ORD record
ord-ad343ad3024443c09bc66d9b2a18bcb8
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05212042

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes