Benzoyl chloride, 3-chloro- → 6-[4-(3-Chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649209

Reaktionsgleichung

Reaktionsgleichung von HRID 1649209
Br.[N:2]1([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].N1(C2C=C3C(=CC=2)NC(=O)CC3)CCNCC1.[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45](Cl)=[O:46]>CN(C=O)C.O.C(N(CC)CC)C>[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45]([N:5]1[CH2:6][CH2:7][N:2]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH2:3][CH2:4]1)=[O:46]

Komponenten

8

Edukt 4

HCID 69252Benzoyl chloride, 3-chloro-HCID 516892Sodium BicarbonateHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 132363086-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromide

Produkt 1

HCID 132363246-[4-(3-Chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyrilAusbeute 35,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

6-(1-Piperazinyl)-3,4-dihydrocarbostyril monohydrobromide (1 g) was suspended in 15 ml of DMF. After adding 296 mg of sodium hydrogencarbonate, the suspension was stirred at room temperature for 30 minutes to convert the starting compound to 6-(1-piperazinyl)-3,4-dihydrocarbostyril. Then, to the mixture was added 0.62 ml of triethylamine and the mixture was stirred at room temperature while slowly adding dropwise 5 ml of DMF solution containing 532 mg of m-chlorobenzoyl chloride. After completion of addition the reaction mixture was stirred for at room temperature 1 hour. 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 to give 0.4 g of 6-[4-(3-chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 197°-197.5° C., colorless scales.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-0adb51efa4434b288b741add56e93f20
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04415572

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