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

HRID 2417719노트

반응식

HRID 2417719 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 6342Acetonitrile용매

실험 절차

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 filitrate 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°.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. filtrationfiltered
  4. washThe filitrate 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

출처 및 근거

ORD 기록
ord-d974975d2105440ea214f88007f94b20
출처 데이터셋
uspto-grants-1984_09
특허 번호
US04469869

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