Water → 1-(4-Nitrobenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]3,4-dihydrocarbostyril

HRID 845744

Reaktionsgleichung

Reaktionsgleichung von HRID 845744
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)[CH2:10][CH2:9]1)=[O:7].C([Li])CCC.[N+:35]([C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)([O-:37])=[O:36].O>O1CCCC1>[N+:35]([C:38]1[CH:39]=[CH:40][C:41]([C:42]([N:20]2[C:21]3[C:16](=[CH:15][C:14]([N:11]4[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]5[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:3]([O:2][CH3:1])[CH:4]=5)[CH2:13][CH2:12]4)=[CH:23][CH:22]=3)[CH2:17][CH2:18][C:19]2=[O:24])=[O:43])=[CH:45][CH:46]=1)([O-:37])=[O:36]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5663VesnarinoneHCID 85024-Nitrobenzoyl chlorideHCID 178418339Butyllithium

Produkt 1

HCID 141806831-(4-Nitrobenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]3,4-dihydrocarbostyrilAusbeute 18,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (10 g) in anhydrous tetrahydrofuran (250 ml) was added slowly n-butyllithium (20 ml, 1.5N hexane solution) with stirring and under ice-cooling. After completion of addition, the mixture was stirred at room temperature for 2 hours. Then, to the mixture was added slowly a solution of p-nitrobenzoyl chloride (6.1 g) in anhydrous tetrahydrofuran (25 ml) with stirring and under ice-cooling. After completion of addition, the mixture was stirred at the same temperature for 30 minutes. After completion of reaction, the reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed successively with water and saturated saline solution and dried over magnesium sulfate. The choloroform extract was evaporated under reduced pressure and the resultant residue was purified by silica-gel column chromatography (eluent:dichloromethane:methanol=100:1) to give 1-(4-nitrobenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]3,4-dihydrocarbostyril (2.6 g).

Aufarbeitung

  1. temperaturecooling
  2. additionAfter completion of addition
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. stirringwith stirring and under ice-
  5. temperaturecooling
  6. additionAfter completion of addition
  7. stirringthe mixture was stirred at the same temperature for 30 minutes
  8. customAfter completion of reaction
  9. extractionextracted with chloroform
  10. washThe chloroform layer was washed successively with water and saturated saline solution
  11. dry with materialdried over magnesium sulfate
  12. extractionThe choloroform extract
  13. customwas evaporated under reduced pressure
  14. customthe resultant residue was purified by silica-gel column chromatography (eluent:dichloromethane:methanol=100:1)

Quellen und Nachweise

ORD-Eintrag
ord-23b6e0bfb974462d93943d8f3ecbc4d3
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04760064

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