Potassium Iodide → HCID 13078406, compound

HRID 223260Notes

Reaction equation

HRID 223260 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:6]=2[CH:16]=1.Cl[CH2:18][CH2:19][CH2:20][N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[NH:23][C:22]1=[O:30].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(CC(=O)C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][N:21]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[NH:23][C:22]4=[O:30])[CH2:14][CH2:15]3)[C:6]=2[CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 27947555-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole

Product 1

HCID 13078406HCID 13078406, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.9 g of 5-fluoro-3-(4-piperidyl)-1,2-benzisoxazole, 3.8 g of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one, 2.7 g of sodium carbonate, a few crystals of potassium iodide and 140 ml of 2-methyl-4-pentanone was stirred and was heated under reflux under nitrogen for 8 hrs. After stirring at ambient temperature for 12 hrs, the mixture was filtered and the filter cake was stirred with 200 ml of water. The solid was collected and dried. Recrystallization from methanol-dimethylformamide-water gave 2.5 g (35.8%) of product. The product was combined with 1.0 g of that from another run to yield a total of 3.5 g of product, mp 202°-204°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 8 hrs
  3. filtrationthe mixture was filtered
  4. stirringthe filter cake was stirred with 200 ml of water
  5. customThe solid was collected
  6. customdried
  7. customRecrystallization from methanol-dimethylformamide-water

Sources & evidence

ORD record
ord-8e1307a36c514b7da7d1b2f7684cdf0d
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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