Triethylamine → 8-[4-(2-Chlorobenzoyl)-1-piperazinyl]carbostyril

HRID 1649258Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1649258
[N:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[NH:15][C:14](=[O:17])[CH:13]=[CH:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29]>CN(C=O)C.C(=O)([O-])O.[Na+]>[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[NH:15][C:14](=[O:17])[CH:13]=[CH:12]3)[CH2:2][CH2:3]1)=[O:29]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 132363748-(1-Piperazinyl)carbostyril

Produkt 1

HCID 132363718-[4-(2-Chlorobenzoyl)-1-piperazinyl]carbostyrilAusbeute 28,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel2×

Versuchsvorschrift

8-(1-Piperazinyl)carbostyril (0.7 g, 2.26 mmols) and sodium hydrogencarbonate (0.2 g) were suspended in 5 ml of DMF and the suspension was stirred at room temperature for 30 minutes. To the resulting mixture was added 0.4 ml of triethylamine, and further a solution of 0.47 g of 2-chlorobenzoyl chloride in 5 ml of DMF dropwise, followed by stirring at room temperature for 30 minutes. The reaction mixture was poured in saturated aqueous sodium hydrogencarbonate and extracted with chloroform. The organic layer was washed with water and then with saturated aqueous sodium hydrogencarbonate and dried over sodium sulfate. After distilling off the solvent, ether was added to the residue to crystallize. The crystals thus obtained were recrystallized from ethanol to give 0.24 g of 8-[4-(2-chlorobenzoyl)-1-piperazinyl]carbostyril, m.p. 239°-240.5° C., colorless needles.

Aufarbeitung

  1. stirringby stirring at room temperature for 30 minutes
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialwith saturated aqueous sodium hydrogencarbonate and dried over sodium sulfate
  5. distillationAfter distilling off the solvent, ether
  6. additionwas added to the residue
  7. customto crystallize
  8. customThe crystals thus obtained
  9. customwere recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-db40090d663b45f2b8040c7dac869dd9
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04415572

Notizen zur Reaktion

Wird geladen…