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Ethyl Acetate → Deacetyldiltiazem hydrochloride

HRID 1903702
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1903702
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][Cl:27].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[ClH:27].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:7][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-HCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Produkt 1

HCID 12449428Deacetyldiltiazem hydrochlorideAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 30.1 g of cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one, 18.7 g of 2-(dimethylamino)ethyl chloride hydrochloride, 33.0 g of potassium carbonate and 240 ml of ethyl acetate is refluxed for 30 minutes under stirring. Then, 5 ml of water are added to the mixture, and the aqueous mixture is further refluxed for 6 hours under stirring. After cooling the reaction mixture, said mixture is washed with water. The ethyl acetate layer is separated and washed with water. The ethyl acetate layer is then evaporated under reduced pressure to remove ethyl acetate. The residue is dissolved in ethanol. After cooling the solution, said solution is acidified with 10% HCl/ethanol and then stirred at a temperature below 10° C. for 5 hours. The crystalline precipitates are collected by filtration, washed with ethanol and then dried. 37.9 g of cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepine-4(5H)-one hydrochloride are thereby obtained. Yield: 92.7%

Aufarbeitung

  1. temperatureis refluxed for 30 minutes
  2. temperaturethe aqueous mixture is further refluxed for 6 hours
  3. stirringunder stirring
  4. temperatureAfter cooling the reaction mixture
  5. washis washed with water
  6. customThe ethyl acetate layer is separated
  7. washwashed with water
  8. customThe ethyl acetate layer is then evaporated under reduced pressure
  9. customto remove ethyl acetate
  10. dissolutionThe residue is dissolved in ethanol
  11. temperatureAfter cooling the solution
  12. stirringstirred at a temperature below 10° C. for 5 hours
  13. customThe crystalline precipitates
  14. filtrationare collected by filtration
  15. washwashed with ethanol
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c7166a5db9a448348de3500484cd35c2
Quelldatensatz
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04438035

Notizen zur Reaktion

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