1-Benzyl-4-(4-nitrophenyl)piperazine → 4-(4-Benzylpiperazin-1-yl)aniline

HRID 479379

Reaction equation

HRID 479379 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-]>O.C(O)C.C(O)(=O)C.[Zn]>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineHCID 5284359Calcium Chloride

Product 1

HCID 7372594-(4-Benzylpiperazin-1-yl)anilineYield 96.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 86584229Acetic acid ethanol waterSolvent

Procedure

4-(4-Benzyl-1-piperazinyl)-1-nitrobenzene (2.6 g; 8.9 mmol) synthesized by the above process and zinc powder (3.2 g; 48 mmol) were added to a solution of calcium chloride (665 mg; 6.0 mmol) in water-ethanol-acetic acid (12 ml-55 ml-1.2 ml), and the mixture was stirred under reflux for 15 minutes in a bath controlled at 110° C. Insoluble substances were removed from the reaction mixture by suction filtration through Celite, and the filtrate was concentrated under reduced pressure. A saturated aqueous solution of sodium hydrogencarbonate was added to the resultant concentrated residue to conduct extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The thus-obtained crude crystals were recrystallized from benzene-n-hexane to obtain 2.3 g (yield: 96%) of 4-(4-benzyl-1-piperazinyl)aniline as pale brown needles (melting point: 137-138° C.).

Workup

  1. temperatureunder reflux for 15 minutes in a bath
  2. customcontrolled at 110° C
  3. customInsoluble substances were removed from the reaction mixture by suction filtration through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionA saturated aqueous solution of sodium hydrogencarbonate was added to the resultant concentrated residue
  6. extractionextraction with chloroform
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe thus-obtained crude crystals
  10. customwere recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-eb341ba792304dabbe20cdd9ec0a2ed7
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Linked notes

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