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Potassium Carbonate → 1-Acetyl-4-(3-amino-4-nitrophenyl)piperazine

HRID 349663
Notes
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Reaction equation

HRID 349663 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.[C:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:12]([N:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 837951-Acetylpiperazine

Product 1

HCID 31168291-Acetyl-4-(3-amino-4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (5 g, 29 mmol), 1-acetylpiperazine (29 mmol), and K2CO3 (4.0 g, 29 mmol) in DMF (20 mL) was stirred at 120° C. for 4 h. The reaction mixture was cooled to room temperature and poured into ice cold water (100 mL). The crude solid product was collected by filtration, air dried, and purified by flash chromatography (silica gel, 4×15 cm, eluted with CHCl3) to yield the product as orange crystals.

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 flash chromatography (silica gel, 4×15 cm, eluted with CHCl3)

Sources & evidence

ORD record
ord-cf6b38e662d047fca0f815c59f99da37
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