Potassium Iodide → HCID 13076453, compound

HRID 370904Notes

Reaction equation

HRID 370904 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[I-].[K+].[CH:23]1([CH2:26][Cl:27])[CH2:25][CH2:24]1>CN(C)C=O.CCOCC.[Cl-].[Na+]>[ClH:27].[CH:23]1([CH2:26][N:1]2[CH2:2][CH2:3][CH:4]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][N:8]=3)[CH2:5][CH2:6]2)[CH2:25][CH2:24]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 80013(Chloromethyl)cyclopropaneHCID 516892Sodium BicarbonateHCID 130764363-(Piperidin-4-yl)benzo[d]isoxazole

Product 1

HCID 13076453HCID 13076453, compoundYield 48.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 5.0 g of 3-(4-piperidyl)-1,2-benzisoxazole, 5.5 g of sodium bicarbonate and 3.0 g of potassium iodide in 75 ml of dimethylformamide was added, dropwise, 2.4 g of cyclopropylmethyl chloride in 25 ml of dimethylformamide, with stirring. The reaction was stirred at 80° for 20 hrs, cooled to room temperature and filtered. The filtrate was poured into 1 l of water and extracted with ether (three times). The ether extracts were washed with saturated sodium bicarbonate solution, saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed to give an oil, which was dissolved in ether into which sodium chloride was bubbled. The precipitate was collected and recrystallized twice from ethanol to give 3.5 g of product, mp, 234.5°-236°.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. additionThe filtrate was poured into 1 l of water
  4. extractionextracted with ether (three times)
  5. washThe ether extracts were washed with saturated sodium bicarbonate solution, saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customto give an oil, which
  9. customwas bubbled
  10. customThe precipitate was collected
  11. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-e0604b6ac1314bbcacf76265ffabfe2a
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

Loading…