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

HRID 728813Notes

Reaction equation

HRID 728813 reaction equation
O.O.[Sn](Cl)(Cl)(Cl)Cl.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)([O-])=O>C(O)C>[C:24]1([CH2:23][N:20]2[CH2:19][CH2:18][N:17]([C:14]3[CH:13]=[CH:12][C:11]([NH2:8])=[CH:16][CH:15]=3)[CH2:22][CH2:21]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 7372594-(4-Benzylpiperazin-1-yl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 474 g (2.10 mol) tin chloride dihydrate to a refluxing solution of 125 g (0.420 mol) 4-(4-nitrophenyl)-1-(phenylmethyl)piperazine in ethanol. Reflux the solution for about 15 h then cool to room temperature and remove the solvent. Dissolve the residue in water and adjust to pH 12 withsodium hydroxide. Extract the aqueous solution with methylene chloride and dry the organic layer with anhydrous sodium sulfate. Concentration at reduced pressure gives the title compound.

Workup

  1. temperatureReflux the solution for about 15 h
  2. customremove the solvent
  3. dissolutionDissolve the residue in water
  4. extractionExtract the aqueous solution with methylene chloride
  5. dry with materialdry the organic layer with anhydrous sodium sulfate
  6. concentrationConcentration at reduced pressure

Sources & evidence

ORD record
ord-a6e88dd3930a417ea6dae43e11ad4dec
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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