Benzimidazole → HCID 21071124, compound

HRID 1372132Notes

Reaction equation

HRID 1372132 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH2:22][CH2:21]1)=[O:19]>CN(C=O)C>[N:1]1([CH2:17][C:18]([N:20]2[CH2:21][CH2:22][N:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[CH2:24][CH2:25]2)=[O:19])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 40539571-(Chloroacetyl)-4-(4-chlorophenyl)piperazine

Product 1

HCID 21071124HCID 21071124, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Benzimidazole (0.785 g, 0.7 mmol) was taken in dry DMF (15 ml) and dry potassium carbonate (340 mg) and KI (20 mg) was added to it and the reaction mixture stirred at room temperature for 1 h under nitrogen. 2-Chloro-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone (200 mg, 1.1 mmol) in DMF (5 ml) was then added to the mixture through a syringe. The reaction was then heated at 140° C. for 14 h, cooled and then quenched with water and extracted with ethyl acetate. Drying of the organic layer with Na2SO4 followed by concentration gave material that on purification by flash chromatography (CHCl3/MeOH) afforded pure product: 1H NMR (300 MHz, CDCl3): δ 8.10–7.65 (m, 4H), 7.26 (d, 2H), 6.83 (d, 2H), 4.99 (s, 2H), 3.79–3.66 (m, 4H), 3.14 (br, 4H).

Workup

  1. temperatureThe reaction was then heated at 140° C. for 14 h
  2. temperaturecooled
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialDrying of the organic layer with Na2SO4
  6. concentrationfollowed by concentration
  7. customgave material that
  8. customon purification by flash chromatography (CHCl3/MeOH)
  9. customafforded pure product

Sources & evidence

ORD record
ord-485074b848ae4e75ab8f282eebf06753
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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