Sodium hydride → HCID 20034517, Verbindung

HRID 231076

Reaktionsgleichung

Reaktionsgleichung von HRID 231076
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]([C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1)[CH2:11][CH2:10][CH2:9]2.[Cl:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH3:39])[CH2:28][CH2:27]1>CN(C)C=O>[ClH:22].[ClH:22].[ClH:22].[CH3:39][O:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[N:29]1[CH2:28][CH2:27][N:26]([CH2:25][CH2:24][CH2:23][O:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]([C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=2)[CH2:11][CH2:10][CH2:9]3)[CH2:31][CH2:30]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 6226691-(3-Chloropropyl)-4-(2-methoxyphenyl)piperazineHCID 30187391,2,3,4-Tetrahydro-1-(3-pyridylcarbonyl)quinolin-8-ol

Produkt 1

HCID 20034517HCID 20034517, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

0.53 (11.0 mmol) of a 50% strength sodium hydride dispersion is introduced in portions into a solution of 2.54 g (10.0 mmol) of 8-hydroxy-1-nicotinoyl-1,2,3,4-tetrahydroquinoline in 20 ml of anhydrous dimethylformamide and the mixture is subsequently stirred at 40°-50° C. for 30 minutes. After cooling to room temperature, a solution of 4.03 g (15.0 mmol) of 1-(3-chloropropyl)-4-(2-methoxyphenyl)piperazine in 20 ml of anhydrous dimethylformamide is added dropwise and the mixture is subsequently stirred at room temperature for 16 hours. The reaction solution is poured onto 150 ml of ice-water and extracted with methylene chloride and the extracts are washed several times with water, dried and concentrated. The crude product is further purified by column chromatography on silica gel (mobile phase toluene:ethanol 9:1) and converted into the dihydrochloride as described under Example 2(a). The product thus obtained is identical to the product described under 2(a).

Aufarbeitung

  1. stirringthe mixture is subsequently stirred at room temperature for 16 hours
  2. extractionextracted with methylene chloride
  3. washthe extracts are washed several times with water
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product is further purified by column chromatography on silica gel (mobile phase toluene:ethanol 9:1)
  7. customThe product thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-9393e4b407154a35ba3fa509557bbd05
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845099

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