Potassium Iodide → 4-(4-Chlorophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-1,2,3,6-tetrahydropyridine oxalate

HRID 1462063Notes

Reaction equation

HRID 1462063 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1.Cl[CH2:15][CH2:16][CH2:17][C:18]1[C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[O:20][N:19]=1.[C:28](=[O:31])([OH:30])[O-].[Na+].[I-].[K+].CN(C)C=[O:38]>>[C:21]([OH:20])(=[O:38])[C:28]([OH:30])=[O:31].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][C:18]3[C:22]4[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=4[O:20][N:19]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 133198864-(4-Chlorophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-1,2,3,6-tetrahydropyridine oxalateYield 56%

Conditions

Temperature
80 °C

Procedure

To 35 ml of dry dimethylformamide was added, 3.7 g of 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine, 4.2 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 10 g of sodium bicarbonate, and a few crystals of potassium iodide. After stirring at 80° C. for one hr, the mixture was cooled, 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/ethyl acetate. The organic extract was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvents were evaporated to an oil. The oil was dissolved in ether, filtered and treated with ethereal oxalic acid solution to give 5.2 g (56%) of product, mp 185° C. (dec). Two recrystallizations from ethyl acetate/methanol (9:1) gave the analytical sample, mp 207°-209° C. (dec).

Workup

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated to an oil
  4. stirringThe oil was stirred with 100 ml of water for five mins
  5. extractionextracted with ether/ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with water (2×), saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtering
  10. customthe solvents were evaporated to an oil
  11. dissolutionThe oil was dissolved in ether
  12. filtrationfiltered
  13. additiontreated with ethereal oxalic acid solution

Sources & evidence

ORD record
ord-76d370fc66af483fa2f697d3a204e414
Source dataset
uspto-grants-1984_07
Patent number
US04458075

Reaction notes

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