Cyanogen Bromide → HCID 53643109, Verbindung

HRID 1651620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651620
[N:1]#[C:2]Br.[Cl:4][C:5]1[CH2:6][N:7]=[CH:8][C:9]2([CH3:23])[CH:20]([CH3:21])[CH:18]3[CH2:19][C:13]4=[C:14]([N:17]3C)[CH2:15][CH2:16][C:10]2=[C:11]4[CH:12]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:4][C:5]1[CH2:6][N:7]=[CH:8][C:9]2([CH3:23])[CH:20]([CH3:21])[CH:18]3[CH2:19][C:13]4=[C:14]([N:17]3[C:2]#[N:1])[CH2:15][CH2:16][C:10]2=[C:11]4[CH:12]=1

Komponenten

5

Edukt 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 53780973HCID 53780973, Verbindung

Produkt 1

HCID 53643109HCID 53643109, VerbindungAusbeute 162,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 1.68 g of cyanogen bromide and 35 ml of chloroform was added, at room temperature with stirring under nitrogen, a solution of 3.8 g of 10-chloro-1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 100 ml of chloroform. The mixture was heated at reflux for 2 hr, under nitrogen, and cooled to room temperature. Dilute aqueous sodium bicarbonate solution was added and the layers separated. The organic layer was extracted with dilute aqueous sodium bicarbonate solution. The combined aqueous layers were extracted with ether and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate) to afford 6.41 g (78%) of 10-chloro-3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo-[3,2-h][3]benzazocine.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hr, under nitrogen
  3. customthe layers separated
  4. extractionThe organic layer was extracted with dilute aqueous sodium bicarbonate solution
  5. extractionThe combined aqueous layers were extracted with ether
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous potassium carbonate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customthe residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3ccc653f7a334154be4a50026ccd2e34
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04929622

Notizen zur Reaktion

Wird geladen…