Potassium Iodide → Declenperone

HRID 258852Notes

Reaction equation

HRID 258852 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(C)=C)[C:6]1=[O:17].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[NH:7][C:6]3=[O:17])[CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 30173591-(3-Chloropropyl)-1,3-dihydro-3-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 71744DeclenperoneYield 20%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5 parts of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 4.5 parts of (4-fluorophenyl) (4-piperidinyl) methanone, 10 parts of sodium carbonate, 0.2 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. After cooling, the reaction mixture is poured onto water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is taken up in 2-propanone and 2-propanol, previously saturated with gaseous hydrogen chloride, is added. After boiling for 30 minutes, the mixture is evaporated. A diluted hydrochloric acid solution is added to the residue and the whole is stirred and warmed at 40°-45° C for 1 hour. After the addition of 4-methyl-2-pentanone, the mixture is alkalized with ammonium hydroxide and the layers are separated. The organic phase is dried, filtered and and evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 1.5 parts (20%) of 1-{3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 163.9° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. additionthe reaction mixture is poured onto water
  4. customthe layers are separated
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated
  8. addition2-propanol, previously saturated with gaseous hydrogen chloride, is added
  9. customthe mixture is evaporated
  10. additionA diluted hydrochloric acid solution is added to the residue
  11. stirringthe whole is stirred
  12. temperaturewarmed at 40°-45° C for 1 hour
  13. additionAfter the addition of 4-methyl-2-pentanone
  14. customthe layers are separated
  15. customThe organic phase is dried
  16. filtrationfiltered
  17. customevaporated
  18. customThe residue is crystallized from 4-methyl-2-pentanone
  19. filtrationThe product is filtered off
  20. customdried

Sources & evidence

ORD record
ord-83c6375fac394998adf017bd4fab69af
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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