4-Bromoaniline → 1-(4-Bromophenyl)piperazine

HRID 270766Notes

Reaction equation

HRID 270766 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]Cl>C(O)CCC>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 27356291-(4-Bromophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent3×

Procedure

4-Bromo-aniline (2 g, 1.162 mmol) was taken in dry nBuOH (25 mL) and dry potassium carbonate (4.8 g, 34.8 mmol) was added to it and stirred at rt for 1 h under nitrogen. Bis-(2-chloroethyl) amine hydrochloride 2 (2.49 g, 13.9 mmol) in nBuOH (10 mL) was then added to the mixture through a syringe. The reaction mass was then heated at 100° C. for 12 h. nBuOH was evaporated in vacuo and the residue was extracted with ethyl acetate. Drying of the organic layer with Na2SO4 followed by concentration afforded the crude product that on purification silica gel column (chloroform/methanol) afforded the title compound.

Workup

  1. customwas evaporated in vacuo
  2. extractionthe residue was extracted with ethyl acetate
  3. dry with materialDrying of the organic layer with Na2SO4
  4. concentrationfollowed by concentration
  5. customafforded the crude product that
  6. customon purification silica gel column (chloroform/methanol)

Sources & evidence

ORD record
ord-a5921e3da9d84e6bacf3f617b7c3274b
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

Loading…