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

HRID 64619Notes

Reaction equation

HRID 64619 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][CH2:9][CH2:10][CH2:11][C:12]1[C:16]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=2[O:14][N:13]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[ClH:8].[ClH:8].[F:21][C:19]1[CH:18]=[CH:17][C:16]2[C:12]([CH2:11][CH2:10][CH2:9][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[N:13][O:14][C:15]=2[CH:20]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 135207491-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-methylpiperazine dihydrochlorideYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 30 ml of dry dimethylformamide was added 2.0 g of 4-methylpiperazine, 4.2 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 8.0 g of sodium bicarbonate and a few crystals of potassium iodide. After stirring at 100° C. for one and one-half hrs, the mixture was 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 solution was washed with water (2×), saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to an oil, which was dissolved in ether and converted to a salt by treatment with etheral hydrogen chloride. Recrystallization from ethyl acetate/methanol/ether gave 3.2 g (46%) of product, mp 240° C. (dec). Recrystallization from ethyl acetate/methanol/ether gave the analytical sample, mp 245° (dec).

Workup

  1. filtrationthe mixture was filtered
  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. washThe ether solution was washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated to an oil, which
  9. dissolutionwas dissolved in ether
  10. customRecrystallization from ethyl acetate/methanol/ether

Sources & evidence

ORD record
ord-6b1f29dc6360413cb0d83e5b063ea1e9
Source dataset
uspto-grants-1986_09
Patent number
US04609658

Reaction notes

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