Reaktion #804966

Reaktionsgleichung

1-Nitroso-1,2,3,4-tetrahydroquinoline

piperidone

→

product

Ausbeute 81.8%

5,6,8,9,10,11-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline

Ausbeute 81.8%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   Temperaturthe reaction mixture was heated at 85° C. for 1 h
3. 3
   SonstigeAfter completion of reaction
4. 4
   Filtrationthe mixture was filtered
5. 5
   ExtraktionThe mixture was extracted with EtOAc (3×200 mL)
6. 6
   TrocknenThe organic layer was dried over sodium sulfate
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

1-Nitroso-1,2,3,4-tetrahydroquinoline (5.8 g, 0.0357 mol) was dissolved in acetic acid (50 mL). NH-piperidone (7.97 g, 0.0464 mol) was added and cooled to 0° C. Zinc dust was added (11.67 g, 0.1785 mol) in small portions. After addition, the reaction mixture was heated at 85° C. for 1 h. The reaction was monitored by TLC & LCMS. After completion of reaction, the mixture was filtered and the filtrate neutralized by aq. NaHCO3. The mixture was extracted with EtOAc (3×200 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 6.2 g product that was purified by column chromatography using 100-200 mesh silica and 5-7% MeOH in DCM+2 drops NH4OH to give pure product.

Quelle