Water → 5-(4-(2-Methoxyphenyl)-piperazin-1-yl]-2-nitrophenylamine

HRID 884416Notes

Reaction equation

HRID 884416 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.Cl.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochloride

Product 1

HCID 102683335-(4-(2-Methoxyphenyl)-piperazin-1-yl]-2-nitrophenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (1.3 g, 7.0 mmol), 1-(2-methoxyphenyl)-piperazine hydrochloride (5.0 g, 20 mmol), and K2CO3 (4.0 g, 29 mmol) in DMF (20 mL) was stirred at 110° C. for 18 h. The reaction mixture was cooled to room temperature and poured into water (200 mL). The crude solid product was collected by filtration, air dried, and purified by trituration with CHCl3 (1.3 g, 57%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe crude solid product was collected by filtration, air
  3. customdried
  4. custompurified by trituration with CHCl3 (1.3 g, 57%)

Sources & evidence

ORD record
ord-cc9c08a086574f68a5b27b36f961feb8
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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