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

HRID 223575Notes

Reaction equation

HRID 223575 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.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19]Cl.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>C(O)CCC.C(#N)C>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][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

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 444972Fumaric AcidHCID 130764363-(Piperidin-4-yl)benzo[d]isoxazole

Product 1

HCID 130764433-[1-(2-Dimethylaminoethyl)-4-piperidyl]-1,2-benzisoxazole difumarateYield 31.6%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 4.5 g of 3-(4-piperidyl)-1,2-benzisoxazole, 2.6 g of 2-dimethylaminoethyl chloride, 3.0 g of potassium iodide and 5.0 g of potassium carbonate 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 and the solvent was removed under reduced pressure to give an oil. The oil was dissolved in 10 ml of acetonitrile and 3.2 g of fumaric acid was added. The reaction mixture was stirred for 2 hrs, filtered and the filter cake was recrystallized three times from ethanol-ether to give 2.2 g (19.8%) of product, mp, 215°-217°.

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. customthe solvent was removed under reduced pressure
  8. customto give an oil
  9. filtrationfiltered
  10. customthe filter cake was recrystallized three times from ethanol-ether

Sources & evidence

ORD record
ord-4891782c96f842faa3f389ab153f3d4a
Source dataset
uspto-grants-1982_10
Patent number
US04355037

Reaction notes

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