Potassium Iodide → HCID 20385571, compound

HRID 46915Notes

Reaction equation

HRID 46915 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]([CH3:16])=[CH2:15])[C:6]1=[O:17].CC([N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:22]1=[O:36])C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[O:36]=[C:22]1[N:23]([CH2:30][CH2:31][CH2:32][N:33]2[CH2:34][CH2:35][CH:4]([N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[N:7]([CH:14]([CH3:16])[CH3:15])[C:6]3=[O:17])[CH2:3][CH2:2]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[NH:21]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 30173591-(3-Chloropropyl)-1,3-dihydro-3-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 18695994HCID 18695994, compound

Product 1

HCID 20385571HCID 20385571, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.15 parts of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 3.9 parts of 1-(1-methylethyl)-3-(4-piperidinyl)-2H-benzimidazol-2-one, 3.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled to room temperature, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol. The solvent is evaporated and the residue is suspended in water. The suspension is alkalized with a diluted ammonium hydroxide solution and 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 (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 4.2 parts (64%) of 1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-one; mp. 174.3° C.

Workup

  1. temperaturerefluxed overnight
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. stirringThe residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol
  7. customThe solvent is evaporated
  8. extractionthe product is extracted with trichloromethane
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is purified by column-chromatography over silica gel using
  13. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  14. customThe pure fractions are collected
  15. customthe eluent is evaporated
  16. customThe residue is crystallized from 4-methyl-2-pentanone
  17. filtrationThe product is filtered off
  18. customdried

Sources & evidence

ORD record
ord-5d340fceaf9446549cd39fc023f61d83
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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