Water → 5-(4-Methylpiperazin-1-yl)-2-nitroaniline

HRID 349657

Reaction equation

HRID 349657 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 27600345-(4-Methylpiperazin-1-yl)-2-nitroanilineYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (2.5 g, 14 mmol), 1-methylpiperizine (3.2 mL, 30 mmol), and potassium carbonate (K2CO3) (2.0 g, 14 mmol) in dimethylformamide (DMF) (20 mL) was stirred at 120° C. for 18 h. The reaction mixture was cooled to room temperature and poured into water (150 mL). The precipitated crude product was collected by filtration, dried in vacuo, and purified by recrystallization from ethyl acetate (EtOAc) (75 mL) to yield yellow-green crystals (1.8 g, 54%). See, J. Med. Chem., 39:997 (1996).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe precipitated crude product
  3. filtrationwas collected by filtration
  4. customdried in vacuo
  5. custompurified by recrystallization from ethyl acetate (EtOAc) (75 mL)

Sources & evidence

ORD record
ord-c5e3e4baf23b4f81ac13c108ef84a414
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Linked notes

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