Sodium Hydroxide → HCID 13077533, Verbindung

HRID 542849

Reaktionsgleichung

Reaktionsgleichung von HRID 542849
[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Al+3].[Li+].[Cl-].[Cl-].[Cl-].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([NH:23][C:24](=O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2[CH3:37].[OH-].[Na+]>O1CCCC1.O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]3)[CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2[CH3:37]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 166981Aluminum;lithium;tetrachlorideHCID 6451240Aluminum(III) ChlorideHCID 13853361N-(6-Methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide

Produkt 1

HCID 13077533HCID 13077533, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A cold (-40°) slurry of 3.8 g (0.0285 mole) of anhydrous aluminum chloride in 60 ml of tetrahydrofuran was added to an equally cold suspension of 3.2 g (0.087 mole) of lithium aluminum chloride in 40 ml of tetrahydrofuran. The mixture was allowed to warm to -20° and to it was added portionwise a suspension of 7.8 g (0.021 mole) of N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide in 300 ml of tetrahydrofuran. The mixture was allowed to stir overnight as it warmed to room temperature, and then was treated with 13.5 ml of 30% sodium hydroxide solution, and with enough water to clarify the supernatant. The supernatant was separated from the sticky precipiate, concentrated in vacuo to remove most of the tetrahydrofuran, diluted with dichloromethane, washed with water, dried and concentrated to dryness in vacuo. The residue was chromatographed over 200 g of silica gel first with 1 liter of ethyl acetate and then with the following solutions of methanol in ethyl acetate: 5% (1 liter), 10% (1 liter), 15% (1 liter), 20% (1 liter) and 25% (4 liters). The eluant containing product, Rf(silica--75 parts ethyl acetate:25 parts of methanol:1 part triethylamine)=0.05, was concentrated to dryness in vacuo to afford 4.4 g (59%) of the desired product of sufficient purity to use in the next step.

Aufarbeitung

  1. temperatureto warm to -20° and to it
  2. additionwas added portionwise
  3. customThe supernatant was separated from the sticky precipiate,
  4. concentrationconcentrated in vacuo
  5. customto remove most of the tetrahydrofuran
  6. additiondiluted with dichloromethane
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated to dryness in vacuo
  10. customThe residue was chromatographed over 200 g of silica gel first with 1 liter of ethyl acetate
  11. additionThe eluant containing product, Rf(silica--75 parts ethyl acetate:25 parts of methanol:1 part triethylamine)=0.05
  12. concentrationwas concentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b462657679eb40bda3ccc607f1c5c7da
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659708

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