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

HRID 64617

Reaction equation

HRID 64617 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.Cl.Cl.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.[C:31](=[O:34])([O-:33])[O-].[K+].[K+]>[I-].[K+].CN(C)C=O>[C:8]([OH:7])(=[O:18])[C:31]([OH:33])=[O:34].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:28]3[CH2:27][CH2:26][N:25]([C:22]4[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=4)[CH2:30][CH2:29]3)=[N:6][O:7][C:8]=2[CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochlorideHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 135207431-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(4-methoxyphenyl)piperazine oxalateYield 86.6%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 40 ml of dimethylformamide was added 4.3 g 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 4.0 g of 4-(4-methoxyphenyl)piperazine dihydrochloride, 10.0 g of milled potassium carbonate, and 0.01 g potassium iodide. The mixture was stirred at 90° C. for two hrs, cooled, filtered, and the filtrate evaporated to an oil. The oil was stirred with 100 ml of water 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. The precipitate was collected and dried to yield 3.0 g (44%) of product. Two recrystallizations from ethyl acetate/methanol/ether (10:1:5) gave the analytical sample, mp 188°-189° C. (dec).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customthe filtrate evaporated to an oil
  4. stirringThe oil was stirred with 100 ml of water
  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 precipitate was collected
  12. customdried

Sources & evidence

ORD record
ord-ecffbe03e1fc40ea85a730e36c4efda5
Source dataset
uspto-grants-1986_09
Patent number
US04609658

Linked notes

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