Potassium Iodide → 3-[1-(3-Diethylaminopropyl)-4-piperidyl]-1,2-benzisoxazole difumarate

HRID 370899Notes

Reaction equation

HRID 370899 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.[CH2:16]([N:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21]Cl)[CH3:17].[I-].[K+].C(=O)(O)[O-].[Na+].[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36]>C(O)CCC.C(#N)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[CH2:16]([N:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][N:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:5][CH2:6]1)[CH3:17]

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 669183-Chloropropyl(diethyl)amineHCID 444972Fumaric AcidHCID 516892Sodium BicarbonateHCID 130764363-(Piperidin-4-yl)benzo[d]isoxazole

Product 1

HCID 130764413-[1-(3-Diethylaminopropyl)-4-piperidyl]-1,2-benzisoxazole difumarateYield 28.3%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 4.0 g of 3-(4-piperidyl)-1,2-benzisoxazole, 3.2 g of 3-diethylaminopropyl chloride, 3.0 g of potassium iodide and 5.0 g of sodium bicarbonate in 100 ml of butanol was heated under reflux for 2 hrs, cooled to room temperature and filtered. The filtrate was washed with water and extracted with ether (3 times). The ether extracts were dried over anhydrous sodium sulfate, filtered and evaporated to give an oil. The oil was dissolved in 10 ml of acetonitrile and 4.2 g of fumaric acid was added. The mixture was stirred for 2 hrs, filtered and the filter cake was recrystallized three times from ethanol-ether to give 2.8 g (26%) of product, mp 174°-176°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. filtrationfiltered
  4. washThe filtrate was washed with water
  5. extractionextracted with ether (3 times)
  6. dry with materialThe ether extracts were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give an oil
  10. filtrationfiltered
  11. customthe filter cake was recrystallized three times from ethanol-ether

Sources & evidence

ORD record
ord-17ca9f180b994f399d629c61ff4fcd11
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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