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Acetyl chloride → Agomelatine

HRID 243638
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 243638
Cl.[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][CH2:15][NH2:16])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[C:23](Cl)(=[O:25])[CH3:24]>O.ClCCl>[CH3:24][C:23]([NH:16][CH2:15][CH2:14][C:11]1[C:12]2[CH:13]=[C:4]([O:3][CH3:2])[CH:5]=[CH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1)=[O:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 160500552-(7-Methoxynaphthalen-1-yl)ethan-1-amine hydrochloride

Produkt 1

HCID 82148AgomelatineAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

The compound V (6.0 g, 0.03 mol) produced as described above and potassium carbonate (5 g) were added to 20 ml of water and 40 ml of dichloromethane, and stirred for 30 minutes. The aqueous layer was removed. The organic layer was cooled to the temperature of 0° C., and acetyl chloride (7.8 g, 0.1 mol) was added dropwise. A reaction was allowed to proceed at room temperature for 1 hour. 100 ml water was then added, and the reaction solution was extracted with dichloromethane (50 ml*3). The organic phases were combined, dried with anhydrous magnesium sulfate, and filtered to remove the drying agent. The filtrate was concentrated under reduced pressure, to give a solid. The solid was recrystallized in a 2:1 toluene/n-hexane mixture, to produce 4.8 g of agomelatine. The yield was 78.5%. The melting point was 107-108° C. (in Literature [2], 109° C.).

Aufarbeitung

  1. customThe aqueous layer was removed
  2. additionwas added dropwise
  3. waitto proceed at room temperature for 1 hour
  4. extractionthe reaction solution was extracted with dichloromethane (50 ml*3)
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove the drying agent
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a solid
  10. customThe solid was recrystallized in a 2:1 toluene/n-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-8c09a56562a740dd8cdb2680dfc6f064
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08653281B2

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