Ethanol → 4-(4-Benzylpiperazin-1-yl)aniline

HRID 2066701Notes

Reaction equation

HRID 2066701 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.CCO.O>[Fe].CC(O)=O>[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

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 27474271-Benzyl-4-(4-nitrophenyl)piperazine

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (5.4 g, 97 mmol, 4 equiv) is added portionwise to an 80° C. mixture of 1-benzyl-4-(4-nitro-phenyl)-piperazine (7.2 g, 24.2 mmol), EtOH (150 mL), H2O (40 mL), and AcOH (20 mL). The reaction mixture is stirred for 1.75 h at 80° C., allowed to cool to RT, and concentrated. The residue is diluted with EtOAc and an aqueous saturated solution of Na2CO3. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated to afford the title compound: ES-MS: 268.3 [MH]+; single peak at tR=1.30 min (system 1).

Workup

  1. temperatureto cool to RT
  2. concentrationconcentrated
  3. additionThe residue is diluted with EtOAc
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with EtOAc
  6. washThe combined organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-82bfc875fef24eae81fa04f2b06a4e42
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

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