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

HRID 485487Notes

Reaction equation

HRID 485487 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[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:27](=[O:30])([OH:29])[O-].[Na+].[I-].[K+].CN(C)C=[O:37]>>[C:20]([OH:19])(=[O:37])[C:27]([OH:29])=[O:30].[F:26][C:24]1[CH:23]=[CH:22][C:21]2[C:17]([CH2:16][CH2:15][CH2:14][N:10]3[CH2:11][CH2:12][N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:8][CH2:9]3)=[N:18][O:19][C:20]=2[CH:25]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 135207311-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-phenylpiperazine oxalate

Conditions

Temperature
100 °C

Procedure

To 35 ml of dry dimethylformamide was added 1.6 g of 4-phenylpiperazine, 2.1 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 heated at 100° C. for three hrs, with stirring. The mixture was filtered and the filtrate was evaporated to an oil. The oil was stirred with 100 ml of water for five mins and then extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, the solution was converted to 4.0 g (70%) of product, by treatment with ethereal oxalic acid. Recrystallization twice from ethyl acetate/methanol/ether yielded the analytical sample mp 188°-190°]C. (dec).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to an oil
  3. stirringThe oil was stirred with 100 ml of water for five mins
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water (2×), saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customRecrystallization twice from ethyl acetate/methanol/ether
  10. customyielded the analytical sample mp 188°-190°]C

Sources & evidence

ORD record
ord-32d77be5f3974785890404c7aac3c826
Source dataset
uspto-grants-1985_08
Patent number
US04536578

Reaction notes

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