Potassium Iodide → HCID 21973236, compound

HRID 350696Notes

Reaction equation

HRID 350696 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[N:10][N:9]([CH3:12])[C:8](=[O:13])[CH:7]=1.[F:14][C:15]1[CH:29]=[CH:28][C:18]2[C:19]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[N:20][O:21][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[F:14][C:15]1[CH:29]=[CH:28][C:18]2[C:19]([CH:22]3[CH2:23][CH2:24][N:25]([CH2:3][CH2:4][NH:5][C:6]4[CH:11]=[N:10][N:9]([CH3:12])[C:8](=[O:13])[CH:7]=4)[CH2:26][CH2:27]3)=[N:20][O:21][C:17]=2[CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 22339777HCID 22339777, compound

Product 1

HCID 21973236HCID 21973236, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.67 g (16.4 millimoles) of 5-(2-chloroethylamino)-2-methyl-2H-pyridazine-3-one-hydrochloride, 90 ml of acetonitrile, 4.05 g (18.4 millimoles) of 6-fluoro-3-piperidine-4-yl-1,2-benzisoxazole, 6.84 g of potassium carbonate and 0.37 g of potassium iodide are admixed. The reaction mixture is stirred under heating to boiling for 24 hours, cooled to room temperature and filtered. To the product 100 ml of water are added and the aqueous phase is extracted five times with 50.0 ml of dichloro methane each. The united organic phases are washed with water, dried over anhydrous magnesium sulfate, filtered and the organic phase is evaporated in vacuo. The residue is suspended in diethyl ether and filtered. The crude product is recrystallized from acetonitrile. Thus 3.4 g of the desired compound are obtained. Yield 55.9%.

Workup

  1. temperatureunder heating
  2. filtrationfiltered
  3. additionTo the product 100 ml of water are added
  4. extractionthe aqueous phase is extracted five times with 50.0 ml of dichloro methane each
  5. washThe united organic phases are washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe organic phase is evaporated in vacuo
  9. filtrationfiltered
  10. customThe crude product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c1051382d16847cda4ae4bb7953ce608
Source dataset
uspto-grants-2007_02
Patent number
US07183283B2

Reaction notes

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