1-Bromo-4-nitrobenzene → 1-Methyl-4-(4-nitrophenyl)piperazine

HRID 639368Notes

Reaction equation

HRID 639368 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>O>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 114661-Bromo-4-nitrobenzeneHCID 531671-Methylpiperazine

Product 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g (0.247 Mol) of 1-Bromo-4-nitro-benzene and 55 mL. (0.495 Mol) of 1-methyl-piperazine are heated for 26 h at 80° C. After cooling, the reaction mixture is taken up in water and extracted with CH2Cl2CH3OH (8:2). The combined organic layers are dried (Na2SO4), filtered and evaporated under reduced pressure. The crude product is recrystallized from ethanol to obtain 1-methyl-4-(4-nitro-phenyl)-piperazine. Title compound: ES-MS: 443.0 [M+H]+; Rf=0.38 (CH2Cl2/MeOH 9:1).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with CH2Cl2CH3OH (8:2)
  3. dry with materialThe combined organic layers are dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-ee3606618aec4d00a6cd78a10453ddc4
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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