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

HRID 349667
Notes
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Reaction equation

HRID 349667 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-579e613bfeb34d5e8b55a1c38dc40bb2
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179912B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes