Veratroyl chloride → Vesnarinone

HRID 1649208

Reaktionsgleichung

Reaktionsgleichung von HRID 1649208
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.[CH3:41][O:42][C:43]1[CH:44]=[C:45]([CH:49]=[CH:50][C:51]=1[O:52][CH3:53])[C:46](Cl)=[O:47]>CN(C)C=O.C(N(CC)CC)C>[CH3:41][O:42][C:43]1[CH:44]=[C:45]([CH:49]=[CH:50][C:51]=1[O:52][CH3:53])[C:46]([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:47]

Komponenten

7

Edukt 4

HCID 77070Veratroyl chlorideHCID 516892Sodium BicarbonateHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 132363086-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromide

Produkt 1

HCID 5663VesnarinoneAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

6-(1-Piperazinyl)-3,4-dihydrocarbostyril monohydrobromide (3.5 g) was suspended in 40 ml of dimethylformamide (hereafter referred to as DMF for brevity). After adding 960 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 2.34 ml of triethylamine and the mixture was stirred at room temperature while slowly adding dropwise 10 ml of DMF solution containing 2.9 g of 3,4-dimethoxybenzoyl chloride. After completion of addition the reaction mixture was stirred for 30 minutes. The reaction mixture was poured into a large amount of saturated saline solution and extracted with chloroform. The extract was washed with saturated sodium hydrogen carbonate solution and subsequently with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from chloroform-ethanol to give 3.8 g of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 238°-239.5° C., colorless granules.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature
  2. additionAfter completion of addition the reaction mixture
  3. stirringwas stirred for 30 minutes
  4. additionThe reaction mixture was poured into a large amount of saturated saline solution
  5. extractionextracted with chloroform
  6. washThe extract was washed with saturated sodium hydrogen carbonate solution and subsequently with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationChloroform was distilled off
  9. customresidual crystals were recrystallized from chloroform-ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4f6e69d049b24e2c8ea7dcdc12978497
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04415572

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