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Potassium Iodide → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(2-pyridyl)piperazine dihydrochloride

HRID 64879
Notes
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Reaction equation

HRID 64879 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[Cl:13][CH2:14][CH2:15][CH2:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=2[O:19][N:18]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[ClH:13].[ClH:13].[F:26][C:24]1[CH:23]=[CH:22][C:21]2[C:17]([CH2:16][CH2:15][CH2:14][N:10]3[CH2:9][CH2:8][N:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:12][CH2:11]3)=[N:18][O:19][C:20]=2[CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 944591-(2-Pyridyl)piperazineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 135207471-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(2-pyridyl)piperazine dihydrochlorideYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 30 ml of dry dimethylformamide was added 2.45 g of 1-(2-pyridyl)piperazine, 3.4 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 8.0 g of sodium bicarbonate, and a few crystals of potassium iodide. The mixture was stirred at 100° C. for one and one-half hrs, filtered, the filtrate was evaporated to an oil. The oil was stirred with 100 ml water for five mins and extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride and dried over anhydrous magnesium sulfate. After filtering, the solvent was evaporated to an oil, which was dissolved in ether, and converted to a salt by treatment with ethereal hydrogen chloride. The salt was recrystallized from ethyl acetate/methanol/ether to yield 3.0 g (48%) of product. Two recrystallizations from ethyl acetate/methanol/ether gave the analytical sample mp 235°-240° C. (dec).

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated to an oil
  3. stirringThe oil was stirred with 100 ml water for five mins
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water (2×), saturated sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customthe solvent was evaporated to an oil, which
  10. dissolutionwas dissolved in ether
  11. customThe salt was recrystallized from ethyl acetate/methanol/ether

Sources & evidence

ORD record
ord-a7b892b48543477c9760e0435c2c7c4b
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04610988

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes