Dimethylformamide → 1-(4-Methoxyphenyl)-4-(4-nitrophenyl)piperazine

HRID 1154727

Reaction equation

HRID 1154727 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13.4 parts of 1-(4-methoxyphenyl)piperazine dihydrochloride, 7.9 parts of 1-chloro-4-nitrobenzene, 10 parts of potassium carbonate and 90 parts of N,N-dimethylformamide is stirred and refluxed overnight. The reaction mixture is diluted with water and the product is extracted twice with trichloromethane. The combined extracts are dried, filtered and evaporated. The residue is triturated in 4-methyl-2-pentanone. The product is filtered off and crystallized from 1,4-dioxane, yielding 10.5 parts (67%) of 1-(4-methoxyphenyl)-4-(4-nitrophenyl)piperazine; mp. 195.1° C.

Workup

  1. temperaturerefluxed overnight
  2. extractionthe product is extracted twice with trichloromethane
  3. customThe combined extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is triturated in 4-methyl-2-pentanone
  7. filtrationThe product is filtered off
  8. customcrystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-5a7c8710c45e4270a123e201951785e5
Source dataset
uspto-grants-1984_12
Patent number
US04490530

Linked notes

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