Potassium Iodide → HCID 21973227, compound

HRID 350697Notes

Reaction equation

HRID 350697 reaction equation
Cl.Cl[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[N:11][N:10]([CH3:13])[C:9](=[O:14])[CH:8]=1.[F:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:21][O:22][C:18]=2[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[F:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([CH:23]3[CH2:24][CH2:25][N:26]([CH2:3][CH2:4][CH2:5][NH:6][C:7]4[CH:12]=[N:11][N:10]([CH3:13])[C:9](=[O:14])[CH:8]=4)[CH2:27][CH2:28]3)=[N:21][O:22][C:18]=2[CH:17]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 21973229HCID 21973229, compound

Product 1

HCID 21973227HCID 21973227, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.12 g (17.3 millimoles) of 5-(3-chloropropylamino)-2-methyl-2H-pyridazine-3-one-hydrochloride, 100 ml of acetonitrile, 4.29 g (19.5 millimoles) of 6-fluoro-3-piperidine-4-yl-1,2-benzisoxazole, 7.24 g of potassium carbonate and 0.39 g of potassium iodide are admixed. The reaction mixture is heated to boiling under stirring 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 90 ml of dichloro methane each. The united organic phases are washed with a saturated sodium chloride solution; dried over magnesium sulfate and filtered over activated charcoal. The organic filtrate is evaporated in vacuo. The residue is suspended in diethyl ether and filtered. The crude product is recrystallized from acetonitrile. Thus 4.14 g of the desired compound are obtained. Yield 62.2%. M.p.: 163–165° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. filtrationfiltered
  3. additionTo the product 100 ml of water are added
  4. extractionthe aqueous phase is extracted five times with 90 ml of dichloro methane each
  5. washThe united organic phases are washed with a saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered over activated charcoal
  8. customThe organic filtrate is evaporated in vacuo
  9. filtrationfiltered
  10. customThe crude product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-253581045e154580bbf9b9d394fe501a
Source dataset
uspto-grants-2007_02
Patent number
US07183283B2

Reaction notes

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