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

HRID 450048Notes

Reaction equation

HRID 450048 reaction equation
Cl[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.C(N(C(C)C)C(C)C)C>C1COCC1>[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

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 531671-MethylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazineYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-chloro-4-nitro benzene (3 g, 19 mmol), 1-methyl piperazine (2.28 g, 22.8 mmol) and ethyl-diisopropylamine (2 ml) in THF (20 ml) was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure to give a residue, which was then partitioned between dichloromethane and water. The organic layer was separated and evaporated under reduced pressure to give crude compound, which was purified by column chromatography over silica gel, using ethyl acetate as eluent, to yield 1-methyl-4-(4-nitro-phenyl)-piperazine (1.8 g, 44%) as solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residue, which
  3. customwas then partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. customevaporated under reduced pressure
  6. customto give crude compound, which
  7. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-eb83a3f6470242068633a910954d6262
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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