Potassium Iodide → HCID 13207818, compound

HRID 1649368Notes

Reaction equation

HRID 1649368 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:16][CH2:17][CH2:18][C:19]1[C:23]2[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=2[O:21][N:20]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:9][CH2:10][N:11]([CH2:16][CH2:17][CH2:18][C:19]3[C:23]4[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=4[O:21][N:20]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 13207818HCID 13207818, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 30 ml of dry dimethylformamide was added 3.0 g of 4-(4-chlorophenyl)-4-hydroxypiperidine, 2.99 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 8.0 g of sodium bicarbonate, and a crystal of potassium iodide. After stirring at 90° C. for one hr, the mixture was evaporated to an oil. The oil was stirred with 100 ml of water for five mins, and then extracted with ether. The ether solution was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent was evaporated. Recrystallization of the residue from ethyl ether gave 3.6 g of product, mp 142°-145° C. The analytical sample was obtained by recrystallization from ethyl and had mp 148°-150° C.

Workup

  1. customthe mixture was evaporated to an oil
  2. stirringThe oil was stirred with 100 ml of water for five mins
  3. extractionextracted with ether
  4. washThe ether solution was washed with water (2×), saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customthe solvent was evaporated
  8. customRecrystallization of the residue from ethyl ether

Sources & evidence

ORD record
ord-ef2d767bfcef4273b6d16cc4e5da7f66
Source dataset
uspto-grants-1983_11
Patent number
US04416887

Reaction notes

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