Sodium Chloride → 1-methyl-4-[(7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizin-10-yl)carbonyl]piperazine

HRID 1109586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109586
[O:1]=[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([C:18]([OH:20])=O)=[C:8]2[N:3]1[CH:4]=[CH:5][C:6]1[CH:23]=[CH:22][S:21][C:7]=12.S(Cl)(Cl)=O.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[Cl-].[Na+]>O1CCOCC1.O>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:18]([C:9]2[CH:10]=[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:2](=[O:1])[N:3]3[C:8]=2[C:7]2[S:21][CH:22]=[CH:23][C:6]=2[CH:5]=[CH:4]3)=[O:20])[CH2:31][CH2:30]1

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 24386Thionyl ChlorideHCID 531671-MethylpiperazineHCID 146667437-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylic acid

Produkt 1

HCID 147700761-methyl-4-[(7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizin-10-yl)carbonyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1.93 g of 7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylic acid were converted into the acid chloride with 2.65 ml of thionyl chloride as described. This acid chloride was taken up in 80 ml of dioxane, treated with 2.7 ml of N-methylpiperazine, and the mixture was then stirred at room temperature until the reaction was completed and poured into 200 ml of water. The aqueous phase was saturated with sodium chloride and extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. By recrystallization from toluene there was obtained 1-methyl-4-[(7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizin-10-yl)carbonyl]piperazine as yellow crystals of m.p. 233°-234° (dec.).

Aufarbeitung

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customBy recrystallization from toluene

Quellen und Nachweise

ORD-Eintrag
ord-90649e53c96d4904970c7121eb0edaca
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05321021

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