1-Chloro-4-nitrobenzene → 1-(4-Methoxyphenyl)-4-(4-nitrophenyl)piperazine

HRID 266060

Reaction equation

HRID 266060 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 2697221-(4-Methoxyphenyl)piperazine

Product 1

HCID 51346571-(4-Methoxyphenyl)-4-(4-nitrophenyl)piperazineYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-methoxyphenyl)piperazine dihyclrochloride (0.050 mol), 1-chloro-4-nitrobenzene (0.050 mol) and potassium carbonate (10.0 g) in N,N-dimethylform-amide (100 ml) was stirred and refluxed overnight. The reaction mixture was diluted with water and extracted twice with trichloromethane. The organic layers were combined, dried (MgSO4), filtered and evaporated in vacuum. The residue was successively triturated in 4-methyl-2-pentanone and recrystallized from 1,4-dioxane. The product was filtered off and dried, yielding 10.5 g (67%) of 1-(4-methoxyphenyl)-4-(4-nitrophenyl)-piperazine; mp. 195.1° C. (interm. 1).

Workup

  1. temperaturerefluxed overnight
  2. extractionextracted twice with trichloromethane
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuum
  6. customThe residue was successively triturated in 4-methyl-2-pentanone
  7. customrecrystallized from 1,4-dioxane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-8ff926236b0348718f1a82d2869d7a1d
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Linked notes

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