Potassium Iodide → HCID 21109893, compound

HRID 1766195Notes

Reaction equation

HRID 1766195 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9](=[O:14])[CH2:10][CH2:11][CH2:12][Cl:13])=[CH:4][C:3]=1[Br:15].[NH:16]1[CH2:21][CH2:20][CH:19]([N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[NH:24][C:23]2=[O:31])[CH2:18][CH2:17]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(CC(C)C)=O>[ClH:13].[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9](=[O:14])[CH2:10][CH2:11][CH2:12][N:16]2[CH2:17][CH2:18][CH:19]([N:22]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[NH:24][C:23]3=[O:31])[CH2:20][CH2:21]2)=[CH:4][C:3]=1[Br:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 21109900HCID 21109900, compound

Product 1

HCID 21109893HCID 21109893, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 30.6 g (0.0861 mol) of 1-(4-amino-3,5-dibromophenyl)-4-chloro-1-butanone, 18.6 g (0.0856 mol) of 1-(4-piperidinyl)-1,3-dihydro-2(2H)-benzimidazolone, 18.2 g (0.172 mol) of anhydrous sodium carbonate, 2.0 g of potassium iodide and 800 ml of methylisobutylketone was refluxed for 130 hours. After cooling the mixture was extracted once with 500 ml of water, the organic phase was dried over sodium sulphate and concentrated by evaporation in vacuo. The residue was dissolved in 50 ml of anhydrous ethanol and the equivalent amount of ethanolic hydrogen chloride solution was added dropwise. After standing for 24 hours at ambient temperature the colourless crystals precipitated were suction filtered and dried in vacuo. Yield: 27.0 g (55% of theoretical). M.p.: 297–299 C (decomp.) (ethanol/water 95/5 v/v). Rf 0.21 (El A). C22H24Br2N4O2*HCl (572.73) Calc.: C, 46.14; H, 4.40; Br, 27.90; Cl, 6.19; N, 9.78; Found: 45,10, 4.92, 27.65, 6.09, 9.95

Workup

  1. temperaturewas refluxed for 130 hours
  2. temperatureAfter cooling the mixture
  3. extractionwas extracted once with 500 ml of water
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. dissolutionThe residue was dissolved in 50 ml of anhydrous ethanol
  7. additionthe equivalent amount of ethanolic hydrogen chloride solution was added dropwise
  8. customthe colourless crystals precipitated
  9. filtrationwere suction filtered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-4f6b2d5edab14ae1a57a5039b988d2d6
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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