Potassium Carbonate → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3-methoxyphenyl)piperazine oxalate

HRID 64616Notes

Reaction equation

HRID 64616 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1.Cl[CH2:18][CH2:19][CH2:20][C:21]1[C:25]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:24]=2[O:23][N:22]=1.[C:31](=[O:34])([O-:33])[O-].[K+].[K+]>[I-].[K+].CN(C)C=O>[C:5]([OH:4])(=[O:23])[C:31]([OH:33])=[O:34].[F:30][C:28]1[CH:27]=[CH:26][C:25]2[C:21]([CH2:20][CH2:19][CH2:18][N:14]3[CH2:15][CH2:16][N:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=4)[CH2:12][CH2:13]3)=[N:22][O:23][C:24]=2[CH:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 814291-(3-Methoxyphenyl)piperazine dihydrochlorideHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 135207411-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3-methoxyphenyl)piperazine oxalateYield 82.8%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 40 ml of dimethylformamide was added 5.3 g of 4-(3-methoxyphenyl)piperazine dihydrochloride, 6.4 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 10.0 g of milled potassium carbonate, and 0.01 g of potassium iodide. The mixture was stirred at 90° C. for two hrs, cooled, filtered, and evaporated to an oil. The oil was stirred with 100 ml water for ten mins, and extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, ethereal oxalic acid was added and the resulting precipitate was collected and dried to give 3.8 g (41%) of product. Two recrystallizations from ethyl acetate/methanol/ether (10:1:5), gave the analytical sample, mp 168° C. (dec).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customevaporated to an oil
  4. stirringThe oil was stirred with 100 ml water for ten mins
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with water (2×), saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtering
  10. additionethereal oxalic acid was added
  11. customthe resulting precipitate was collected
  12. customdried

Sources & evidence

ORD record
ord-b9ac73966ecc4a7faee5ba88f6ef6d49
Source dataset
uspto-grants-1986_09
Patent number
US04609658

Reaction notes

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