Calcium Chloride → 4-[3-(1H-Imidazol-1-yl)propyl]aniline

HRID 856727Notes

Reaction equation

HRID 856727 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[N:13]1([CH2:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 101052881-[3-(4-nitrophenyl)propyl]imidazole

Product 1

HCID 214815934-[3-(1H-Imidazol-1-yl)propyl]anilineYield 73.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[3-(4-nitrophenyl)propyl]imidazole (1.2 g) was dissolved in 85% ethanol solution (37 ml), calcium chloride (0.30 g) and reduced iron (1.5 g) were added to the mixture, and the mixture was heated to reflux for 4 hours. After cooling to room temperature, the mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[3-(imidazol-1-yl)propyl]aniline (0.77 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe mixture was filtered with Celite
  4. washwashed with ethyl acetate
  5. customThe solvent was removed under reduced pressure, and water
  6. additionwas added to the obtained residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a3f6a8451ea44fd6b3978e1f88949799
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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