Potassium Carbonate → HCID 21070994, compound

HRID 270917Notes

Reaction equation

HRID 270917 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:7])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)=[O:17]>CN(C=O)C>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([N:21]2[CH2:20][CH2:19][N:18]([C:16](=[O:17])[CH2:15][N:3]3[CH:4]=[C:5]([CH3:7])[N:6]=[C:2]3[CH3:1])[CH2:23][CH2:22]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 40539571-(Chloroacetyl)-4-(4-chlorophenyl)piperazineHCID 178430880HCID 178430880, compound

Product 1

HCID 21070994HCID 21070994, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2,4-dimethylimidazole (0.633 g, 0.7 mmol) was taken up in dry DMF (15 ml) and dry potassium carbonate (340 mg) and KI (20 mg) was added and the reaction mixture was 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 quenched with water and extracted with ethyl acetate. Drying of the organic layer with Na2SO4 followed by concentration gave material that was purified on a silica gel column (CHCl3/MeOH): 1H NMR (300 MHz, CDCl3): δ 7.25 (d, 2H), 6.80 (d, 2H), 6.53 (s, 1H), 4.62 (s, 2H), 3.78 (br, 2H), 3.59 (br, 2H), 3.21 (br, 4H), 2.31 (s, 3H), 2.17 (s, 1H).

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. customwas purified on a silica gel column (CHCl3/MeOH)

Sources & evidence

ORD record
ord-4393d85e1b194925a3bbd949b0817fd6
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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