1-Bromo-4-nitrobenzene → 1-Benzyl-4-(4-nitrophenyl)piperazine

HRID 409672

Reaction equation

HRID 409672 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl.O>[CH2:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 114661-Bromo-4-nitrobenzeneHCID 759941-Benzylpiperazine

Product 1

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-bromo-4-nitrobenzene (5 g, 24.8 mmol) and 1-benzylpiperazine (8.6 ml, 49.5 mmol, 2 equiv) is heated to 80° C. for 17 h. The reaction mixture is allowed to cool to RT, and is diluted with DCM/H2O. The layers are separated and the aqueous phase is extracted with DCM. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by silica gel column chromatography (Hex/EtOAc, 1:1) affords the title compound as a yellow solid: ESI-MS: 298.3 [MH]+; tR=3.25 min (purity: 100%, system 1).

Workup

  1. temperatureto cool to RT
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted with DCM
  4. washThe combined organic phase is washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by silica gel column chromatography (Hex/EtOAc, 1:1)

Sources & evidence

ORD record
ord-58bd338a40824640897be00271babb1d
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Linked notes

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