Pyridine → n,n-dibenzyl-4-bromoaniline

HRID 1378963Notes

Reaction equation

HRID 1378963 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:23](#N)[CH3:24]>>[Br:7][C:8]1[CH:14]=[CH:13][C:11]([N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:2][C:3]2[CH:24]=[CH:23][CH:6]=[CH:5][CH:4]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 78074-Bromoaniline

Product 1

HCID 285423n,n-dibenzyl-4-bromoaniline

Procedure

Pyridine (56.3 ml, 0.698 mol) is added to a solution of p-bromoaniline (50 g, 0.290 mol) in acetonitrile (500 ml) at 5° C., and benzylbromide (84 ml, 0.698 mol) is then added dropwise. The mixture is stirred overnight at room temperature and then 1 hour under reflux. The acetonitrile is evaporated off and the residue is taken up in dichloromethane. The organic phase is washed with 1N HCl and then saturated NaCl, dried over sodium sulfate and evaporated to give 68.5 g of a mixture of mono- and dibenzylated (50:50) product. The mixture is separated by chromatography on silica (cyclohexane/ethyl acetate, 70:30) and yields the expected product.

Workup

  1. temperature1 hour under reflux
  2. customThe acetonitrile is evaporated off
  3. washThe organic phase is washed with 1N HCl
  4. dry with materialsaturated NaCl, dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2e32a2aab58148248590dbe3a47e6e8d
Source dataset
uspto-grants-1997_09
Patent number
US05670493

Reaction notes

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