Dimethyl Sulfoxide → 6-[4-(4-Bromobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649213

Reaktionsgleichung

Reaktionsgleichung von HRID 1649213
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].CS(C)=O.[Br:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1>O>[Br:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]4)[CH2:2][CH2:3]2)=[O:33])=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl Sulfoxide2×HCID 685154-Bromobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 132363166-[4-(4-Bromobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyrilAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

6-(1-Piperazinyl)-3,4-dihydrocarbostyril (2.6 g) and 1 g of sodium hydrogencarbonate was added to 50 ml of dimethyl sulfoxide and the mixture was stirred with ice cooling while slowly adding dropwise 20 ml of dimethyl sulfoxide solution containing 3.2 g of 4-bromobenzoyl chloride. After completion of addition the reaction mixture was stirred at room temperature for 60 minutes. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from methanol-chloroform to give 0.8 g of 6-[4-(4-bromobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 233°-234.5° C., colorless granules.

Aufarbeitung

  1. additionAfter completion of addition the reaction mixture
  2. stirringwas stirred at room temperature for 60 minutes
  3. extractionextracted with chloroform
  4. washThe extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationChloroform was distilled off
  7. customresidual crystals were recrystallized from methanol-chloroform

Quellen und Nachweise

ORD-Eintrag
ord-8b74e0fe28e6457bb77fe4ce5b6178c6
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04415572

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