Imidazole → 1-(3-Phenylpropyl)-1H-imidazole

HRID 1451353Notes

Reaction equation

HRID 1451353 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[C:8]1([CH2:14][CH2:15][CH2:16]Br)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C=O)C>[C:8]1([CH2:14][CH2:15][CH2:16][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydride

Product 1

HCID 99899801-(3-Phenylpropyl)-1H-imidazoleYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of imidazole (6.808 g, 0.1 mol) in dry DMF (100 ml) at 0° C. under argon was added portionwise 4 g (0.1 mol) of 60% sodium hydride and the mixture was stirred for 30 minutes at room temperature, and cooled to 0° C. To the above mixture was added 3-phenylpropyl bromide (19.91 g, 0.1 mol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was heated on a steam-bath for 4 hours and stirred at room temperature overnight. The solvent was concentrated in vacuo, the residue was partitioned between methylene chloride and water, the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residual oil was dried in vacuo and purified by silica gel column chromatography to afford 16.1 g (86%) of 1-(3-phenylpropyl)imidazole.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. temperatureThe reaction mixture was heated on a steam-bath for 4 hours
  4. stirringstirred at room temperature overnight
  5. concentrationThe solvent was concentrated in vacuo
  6. customthe residue was partitioned between methylene chloride and water
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residual oil was dried in vacuo
  10. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7fe5f447f37b40868ca6be9478104fef
Source dataset
uspto-grants-1997_02
Patent number
US05604224

Reaction notes

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