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

HRID 1195766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195766
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][N:12]1[C:18]2=[C:19]3[C:24](=[N:25][C:26]4=[CH:27][CH:28]=[CH:29][C:16](=[C:17]24)[O:15][CH2:14][C:13]1=O)[CH2:23][CH2:22][CH2:21][CH2:20]3>O1CCCC1>[CH3:11][N:12]1[C:18]2=[C:19]3[C:24](=[N:25][C:26]4=[CH:27][CH:28]=[CH:29][C:16](=[C:17]24)[O:15][CH2:14][CH2:13]1)[CH2:23][CH2:22][CH2:21][CH2:20]3

Komponenten

5

Edukt 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 53993904HCID 53993904, Verbindung

Produkt 1

HCID 538157592,3,9,10,11,12-Hexahydro-1-methyl-1H-quino-[4,3,2-ef][1,4]benzoxazepineAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of lithium aluminum hydride in tetrahydrofuran (1.0M, 15.82 ml) and dry tetrahydrofuran (32 ml) was added aluminum chloride (2.10 g) in portions. The mixture was stirred for five mins, 1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.24 g) was added and the mixture was stirred at room temperature overnight. The reaction mixture was quenched with ethyl acetate (150 ml), 10% sodium hydroxide solution was added, and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was adhered to silica (methanol) and flash chromatographed (30-50% ethyl acetate/Hexane) to yield 3.61 g (89.6%) of product, mp 97°-98° C.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with ethyl acetate (150 ml), 10% sodium hydroxide solution
  3. additionwas added
  4. customthe organic layer was separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (30-50% ethyl acetate/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-95cbb7a7668f4708afa754da845cd9a0
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112829

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