1-Methylpiperazine → 1-methyl-4-(2-nitrophenyl)piperazine

HRID 394491Notes

Reaction equation

HRID 394491 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16]>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 738951-Fluoro-2-nitrobenzene2×

Product 1

HCID 4106401-methyl-4-(2-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask fitted with a condensor and addition funnel, N-methylpiperazine (10.0 grams, 0.1 mol) was stirred while 2-fluoronitrobenzene (14.1 grams, 0.1 mol) was added dropwise under nitrogen. Caution—a vigorous exotherm occurred when approximately 20% of the 2-fluoronitrobenzene had been added. Following completion of the addition (˜30 min.) the reaction was stirred another 60 min. at room temperature, diluted with methylene chloride (100 mL) and washed with saturated aqueous Na2CO3 and saturated aqueous sodium chloride. After drying with MgSO4, the solvent was removed in vacuo to give 2-(4-methylpiperazin-1-yl)-1-nitrobenzene as an orange oil, 20.4 grams. Mass spectrum: 221 (M+), 174 (M-HNO2) 1H-NMR (CDCl3, 300 MHz) δ 7.8-7.0 (4H, m), 3.05 (4H, m), 2.55 (4H, t), 2.3 (3H, s).

Workup

  1. additionwas added dropwise under nitrogen
  2. additionhad been added
  3. additioncompletion of the addition (˜30 min.) the reaction
  4. washwashed with saturated aqueous Na2CO3 and saturated aqueous sodium chloride
  5. dry with materialAfter drying with MgSO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b8ef6127f0604a81ba6d4c9042f5fd00
Source dataset
uspto-grants-2003_08
Patent number
US06602874B2

Reaction notes

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