Potassium Iodide → HCID 13078408, compound

HRID 223261Notes

Reaction equation

HRID 223261 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.Cl[CH2:19][CH2:20][CH2:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[NH:24][C:23]1=[O:31].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(CC(=O)C)C>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:19][CH2:20][CH2:21][N:22]4[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[NH:24][C:23]4=[O:31])[CH2:14][CH2:15]3)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 13076428HCID 13076428, compound

Product 1

HCID 13078408HCID 13078408, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.1 g of 6-methoxy-3-(4-piperidyl)-1,2-benzisoxazole, 3.7 g of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one, 3.1 g of sodium carbonate, a few crystals of potassium iodide and 125 ml of 2-methyl-4-pentanone was stirred and heated under reflux under nitrogen for 16 hrs. The reaction was poured into 300 ml of water, the layers were separated and the aqueous layer was extracted twice with dichloromethane. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate and the solvent removed in vacuo to yield an oil. The oil was triturated with ether and the solid was collected. The solid was recrystallized twice from toluene to yield 2.7 g (37.7%) of product, mp 176°-178°.

Workup

  1. temperatureheated
  2. temperatureunder reflux under nitrogen for 16 hrs
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted twice with dichloromethane
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent removed in vacuo
  8. customto yield an oil
  9. customThe oil was triturated with ether
  10. customthe solid was collected
  11. customThe solid was recrystallized twice from toluene

Sources & evidence

ORD record
ord-a7d5d2f31ef24700b5374174cd288284
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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