Hydrochloric Acid → 3-(1-Allyl-4-piperidyl)-1,2-benzisoxazole hydrochloride

HRID 223577Notes

Reaction equation

HRID 223577 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](Br)[CH:17]=[CH2:18].C(=O)(O)[O-].[Na+].[I-].[K+].[ClH:27]>CN(C)C=O.CCOCC>[ClH:27].[CH2:18]([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)[CH:17]=[CH2:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 130764363-(Piperidin-4-yl)benzo[d]isoxazole

Product 1

HCID 130764513-(1-Allyl-4-piperidyl)-1,2-benzisoxazole hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4.0 g of 3-(4-piperidyl)-1,2-benzisoxazole, 2.6 g of allyl bromide, 5.0 g of sodium bicarbonate, and 3.0 g of potassium iodide in 90 ml of dimethylformamide was stirred at 80° for 20 hrs. The reaction was cooled, filtered and poured into 1 l of water. The mixture was extracted with ether (three times) and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give an oil. The oil was dissolved in a small amount of ether into which hydrochloric acid was bubbled. The precipitate was recrystallized from ethanol-ether (three times) to give 2.4 g of product, mp, 174°-176°.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. additionpoured into 1 l of water
  4. extractionThe mixture was extracted with ether (three times)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give an oil
  8. customwas bubbled
  9. customThe precipitate was recrystallized from ethanol-ether (three times)

Sources & evidence

ORD record
ord-fd4c856bdd334881a85b103538b6656c
Source dataset
uspto-grants-1982_10
Patent number
US04355037

Reaction notes

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