1-(2-Chloro-4-nitrophenyl)-4-(4-nitrophenethyl)piperazine → 4-[4-[2-(4-Aminophenyl)ethyl]-1-piperazinyl]-3-chlorobenzenamine

HRID 2291559Notes

Reaction equation

HRID 2291559 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:13][CH2:12]1>C(O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 1

HCID 212789111-(2-Chloro-4-nitrophenyl)-4-(4-nitrophenethyl)piperazine

Product 1

HCID 212789054-[4-[2-(4-Aminophenyl)ethyl]-1-piperazinyl]-3-chlorobenzenamineYield 70.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Chloro-4-nitrophenyl)-4-(4-nitrophenethyl)piperazine (1.0 g), stannous chloride dihydrate (5.7 g) and ethanol (50 ml) were stirred under reflux for 1.25 hours, the mixture was evaporated to low bulk, and added to aqueous 5% sodium hydroxide (100 ml). The mixture was then extracted three times with dichloromethane and the combined organic extracts were dried (sodium sulphate) and evaporated to yield a yellow oil which solidified: yield of the title compound 0.6 g, m.p. 109°-112°. It was used in the next stage without further purification.

Workup

  1. temperatureunder reflux for 1.25 hours
  2. customthe mixture was evaporated to low bulk
  3. additionadded to aqueous 5% sodium hydroxide (100 ml)
  4. extractionThe mixture was then extracted three times with dichloromethane
  5. dry with materialthe combined organic extracts were dried (sodium sulphate)
  6. customevaporated
  7. customto yield a yellow oil which

Sources & evidence

ORD record
ord-1196c0b0062c44c0b43e7c8b2b6c9c35
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

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