Potassium Carbonate → HCID 6992124, compound

HRID 1899395Notes

Reaction equation

HRID 1899395 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])=[O:4].[O:14]=[C:15]1[N:19]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=2[NH:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:13][C:7]1[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:23]1[CH2:22][CH2:21][CH:20]([N:19]2[C:18]3[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=3[NH:16][C:15]2=[O:14])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 34164012-bromo-N-(2,4-difluorophenyl)acetamide

Product 1

HCID 6992124HCID 6992124, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 g (16 mmol) of the bromoacetanilide from Example I and 4.2 g (19 mmol) of 4-(2-oxo-1-benzimidazolinyl)piperidine in 50 ml of dimethylformamide are stirred at RT for 18 h with 2.6 g (19 mmol) of potassium carbonate. The solid is then filtered off with suction, the filtrate is partitioned between ethyl acetate and water, and the aqueous phase is extracted 3 times with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried (MgSO4) and concentrated. The residue obtained is triturated with ether, and the solid is filtered off and then recrystallized from methanol.

Workup

  1. filtrationThe solid is then filtered off with suction
  2. customthe filtrate is partitioned between ethyl acetate and water
  3. extractionthe aqueous phase is extracted 3 times with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customis triturated with ether
  9. filtrationthe solid is filtered off
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2875453875f84c3795d8e3f1ab29af6e
Source dataset
uspto-grants-1996_11
Patent number
US05571921

Reaction notes

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