Aluminum(III) Chloride → 2,3,9,10,11,12-Hexahydro-1-propyl-1H-quino[4,3,2-ef][1,4]benzoxazepine

HRID 1195769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195769
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([N:14]1[C:20]2=[C:21]3[C:26](=[N:27][C:28]4=[CH:29][CH:30]=[CH:31][C:18](=[C:19]24)[O:17][CH2:16][C:15]1=O)[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:12][CH3:13]>O1CCCC1>[CH2:11]([N:14]1[C:20]2=[C:21]3[C:26](=[N:27][C:28]4=[CH:29][CH:30]=[CH:31][C:18](=[C:19]24)[O:17][CH2:16][CH2:15]1)[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:12][CH3:13]

Komponenten

5

Edukt 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 53716832HCID 53716832, Verbindung

Produkt 1

HCID 540056442,3,9,10,11,12-Hexahydro-1-propyl-1H-quino[4,3,2-ef][1,4]benzoxazepineAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of lithium aluminum hydride in tetrahydrofuran (1.0M, 14.2 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.89 g) in portions. The mixture was stirred for five mins, 1,3,9,10,11,12-hexahydro-1-propyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.2 g) was added, and stirring was continued overnight. The reaction mixture was quenched with ethyl acetate (200 ml), 10% sodium hydroxide solution (200 ml) was added, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was recrystallized from pentane/diethyl ether to yield 2.85 g (71%) of product, mp 74.5°-75.5° C.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe reaction mixture was quenched with ethyl acetate (200 ml), 10% sodium hydroxide solution (200 ml)
  4. additionwas added
  5. customthe organic layer was separated
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was recrystallized from pentane/diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-43b6b7771d3944dc8cca1615c0b14fd9
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112829

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