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Potassium Carbonate → 7-[4-(4-benzisoxazolyl-1-piperidinyl)-butoxy]-3,4-dihydro-2(1H)-quinolinone hydrochloride

HRID 241588
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 241588
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.[NH:18]1[CH2:23][CH2:22][CH:21]([C:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3S[N:25]=2)[CH2:20][CH2:19]1.C(=O)([O-])[O-:34].[K+].[K+].Cl.CCO>C(O)C.CC(C)=O>[ClH:1].[O:34]1[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:24]([CH:21]2[CH2:22][CH2:23][N:18]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]3[CH:16]=[C:15]4[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]4)=[CH:9][CH:8]=3)[CH2:19][CH2:20]2)=[N:25]1
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Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 104674677-(4-Chlorobutoxy)-1,2,3,4-tetrahydroquinolin-2-oneHCID 133240934-(3-Benzisothiazolyl) piperidineHCID 21887872Ethanol hydrochloride

Produkt 1

HCID 671787567-[4-(4-benzisoxazolyl-1-piperidinyl)-butoxy]-3,4-dihydro-2(1H)-quinolinone hydrochlorideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

7-(4-chlorobutoxy)-3,4-dihydro-2(1H)-quinolinone (297 mg, 1 mmol), 3-(4-piperidinyl)-1,2-benzisothiazole (220 mg, 1 mmol), and anhydrous potassium carbonate powder (414 mg, 3.3 mmol) are added to 10 ml and react at reflux for 24 hours. The reaction solution is evaporated to dryness and dispersed with 20 ml of dichloromethane and 20 ml of water respectively. The organic layer is extracted with water (20 ml×2) and saturated saline (20 ml) successively, dried over anhydrous magnesium sulfate, and evaporated to dryness to obtain a light yellow powder, which is dissolved into 5 ml of acetone and stirred in an ice bath to precipitate a white solid. The white solid is filtered, washed with small amount of acetone, and dried to obtain 260 mg of a whiter powder. The whiter powder is dissolved into anhydrous ethanol and thereto is drop-added HCl/EtOH to adjust to pH=2 to precipitate a white deposit, which is filtered out and recrystallized in anhydrous ethanol to obtain 200 mg of a product, with a yield of 44%.

Aufarbeitung

  1. customreact
  2. temperatureat reflux for 24 hours
  3. customThe reaction solution is evaporated to dryness
  4. additiondispersed with 20 ml of dichloromethane and 20 ml of water respectively
  5. extractionThe organic layer is extracted with water (20 ml×2) and saturated saline (20 ml) successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customto obtain a light yellow powder, which
  9. customto precipitate a white solid
  10. filtrationThe white solid is filtered
  11. washwashed with small amount of acetone
  12. customdried
  13. customto obtain 260 mg of a whiter powder
  14. customto precipitate a white deposit, which
  15. filtrationis filtered out
  16. customrecrystallized in anhydrous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-db1f90e93f864f7693a5cfd999412ff1
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08653069B2

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