Cesium carbonate → (2-Fluoro-4-nitrophenyl)-(3-imidazol-1-ylpropyl)amine

HRID 56184Notes

Reaction equation

HRID 56184 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:18]=1[NH2:19]>CN(C=O)C>[N:5]1([CH2:4][CH2:3][CH2:2][NH:19][C:18]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:17]=2[F:16])[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1012542-Fluoro-4-nitroanilineHCID 157536751-(3-chloropropyl)-1H-imidazole

Product 1

HCID 18003903(2-Fluoro-4-nitrophenyl)-(3-imidazol-1-ylpropyl)amineYield 122%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-chloropropyl)-1H-imidazole (1.90 g, 13.14 mmol), cesium carbonate (4.28 g, 13.14 mmol) and a catalytic amount of KI in DMF (30 mL) cooled in an ice-bath was added 2-fluoro-4-nitroaniline (1.38 g, 8.84 mmol) in one portion. At the end of addition, the mixture was refluxed and stirred further for 36 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo. To the residue was added water (50 mL) and the resulting mixture was extracted with DCM (20 mL×2). The combined organic layers were washed with brine (20 mL×2) and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=15:1) to give the title compound as yellow oil (2.85 g, 82%).

Workup

  1. additionAt the end of addition
  2. temperaturethe mixture was refluxed
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. additionTo the residue was added water (50 mL)
  6. extractionthe resulting mixture was extracted with DCM (20 mL×2)
  7. washThe combined organic layers were washed with brine (20 mL×2)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=15:1)

Sources & evidence

ORD record
ord-b4f807d0009f40f88d918075ca635fee
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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