Potassium Iodide → HCID 70601008, compound

HRID 46914

Reaction equation

HRID 46914 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8](C(C)=C)[C:7]1=[O:18].[Cl:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[C:25](=[O:27])[NH:26][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[OH2:18].[Cl:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([CH:28]3[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[NH:8][C:7]4=[O:18])[CH2:32][CH2:33]3)[C:25](=[O:27])[NH:26][C:22]=2[CH:21]=1.[Cl:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([CH:28]3[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[NH:8][C:7]4=[O:18])[CH2:32][CH2:33]3)[C:25](=[O:27])[NH:26][C:22]=2[CH:21]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 130168791-(4-chlorobutyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

Product 1

HCID 70601008HCID 70601008, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 9.25 parts of 1-(4-chlorobutyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 7.55 parts of 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 10.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 18 hours. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is dissolved in 40 parts of ethanol and the solution is acidified with 30 parts of a concentrated hydrochloric acid solution. The whole is stirred for 30 minutes and the solvent is evaporated. The residue is suspended in water and the suspension is alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of N,N-dimethylformamide and water. The product is filtered off and dried, yielding 6.5 parts (46%) of 5-chloro-1-{1-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemihydrate; mp. 258° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureAfter cooling
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue is dissolved in 40 parts of ethanol
  8. stirringThe whole is stirred for 30 minutes
  9. customthe solvent is evaporated
  10. extractionThe product is extracted with trichloromethane
  11. customThe extract is dried
  12. filtrationfiltered
  13. customevaporated
  14. customThe residue is purified by column-chromatography over silica gel using
  15. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  16. customThe pure fractions are collected
  17. customthe eluent is evaporated
  18. customThe residue is crystallized from a mixture of N,N-dimethylformamide and water
  19. filtrationThe product is filtered off
  20. customdried

Sources & evidence

ORD record
ord-d3740ad6dc3e430c8efdebacaa51a76b
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Linked notes

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