Water → 5-(3-Carboxypiperazin-1-yl)-4-chloro-2-nitroaniline

HRID 1064359

Reaction equation

HRID 1064359 reaction equation
[Cl:1][C:2]1[C:8](Cl)=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH:14]1[C:19]([OH:21])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].O>C1(O)CCCCC1>[C:19]([CH:14]1[NH:13][CH2:18][CH2:17][N:16]([C:8]2[C:2]([Cl:1])=[CH:3][C:4]([N+:10]([O-:12])=[O:11])=[C:5]([CH:7]=2)[NH2:6])[CH2:15]1)([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 811494,5-Dichloro-2-nitroanilineHCID 2723758Piperazine-2-carboxylic acid

Product 1

HCID 222729645-(3-Carboxypiperazin-1-yl)-4-chloro-2-nitroanilineYield 72.1%

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2.10 g of 4,5-dichloro-2-nitroaniline and 2.20 g of 2-piperazinecarboxylic acid in 20 ml of cyclohexanol, 4.80 g of sodium carbonate was added, followed by 14 hours' stirring at 150° C. After cooling the reaction liquid to room temperature, water was added and the system was washed with chloroform. The aqueous layer was purified with an ion-exchange resin (Diaion HP-20, Mitsubishi Kasei, eluent: methanol). Upon condensing the fraction containing the object product under reduced pressure, 2.20 g of the title compound was obtained.

Workup

  1. temperatureAfter cooling
  2. customthe reaction liquid to room temperature
  3. washthe system was washed with chloroform
  4. customThe aqueous layer was purified with an ion-exchange resin (Diaion HP-20, Mitsubishi Kasei, eluent: methanol)
  5. customUpon condensing the fraction
  6. additioncontaining the object product under reduced pressure

Sources & evidence

ORD record
ord-5da0a42d4ec442708176b763c252be1f
Source dataset
uspto-grants-2005_11
Patent number
US06969712B2

Linked notes

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