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Benzyl Bromide → HCID 53995652, Verbindung

HRID 981945
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 981945
[CH2:1]([CH:3]1[CH2:9][NH:8][C:7]2=[C:10]3[C:15](=[N:16][C:17]4=[CH:18][CH:19]=[CH:20][C:5](=[C:6]24)[O:4]1)[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH3:2].CC(C)([O-:24])C.[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[CH2:27]([N:8]1[C:7]2=[C:10]3[C:15](=[N:16][C:17]4=[CH:18][CH:19]=[CH:20][C:5](=[C:6]24)[O:4][CH:3]([CH2:1][CH3:2])[C:9]1=[O:24])[CH2:14][CH2:13][CH2:12][CH2:11]3)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 23665647Potassium tert-butoxideHCID 54017563HCID 54017563, Verbindung

Produkt 1

HCID 53995652HCID 53995652, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-ethyl-2,3,9,10,11,12-hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepine (5.0 g) in dry tetrahydrofuran (150 ml) was added potassium t-butoxide (3.0 g). The mixture was stirred for 15 mins, benzyl bromide (3.16 ml) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was heated at reflux for 1.5 hrs, allowed to cool, concentrated and diluted with saturated sodium bicarbonate solution (250 ml). The mixture was extracted twice with ethyl acetate (250 ml), and the organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated. Trituration of the residue first with pentane and then diethyl ether, gave 4.65 g (71%) of 1-benzyl-3-ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1.5 hrs
  4. temperatureto cool
  5. concentrationconcentrated
  6. additiondiluted with saturated sodium bicarbonate solution (250 ml)
  7. extractionThe mixture was extracted twice with ethyl acetate (250 ml)
  8. dry with materialthe organic extracts were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aaefb72635c94730921a48a975e81633
Quelldatensatz
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04994452

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