Reaktion #324520

Reaktionsgleichung

trans-8-chloro-1-(4-isopropoxy-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene hydrochloride

potassium carbonate

2-(bromomethyl)pyridine hydrobromide

→

title compound

Ausbeute 58.0%

trans-8-Chloro-1-(4-isopropoxy-cyclohexyl)-5-pyridin-2-ylmethyl-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzoazulene

Ausbeute 58.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby partitioning between 1 M aqueous sodium hydroxide solution (30 ml) and dichloromethane (30 ml)
2. 2
   SonstigeThe layers were separated
3. 3
   ExtraktionThe aqueous layer was extracted with two 30-ml portions of dichloromethane
4. 4
   TrocknenThe combined organic layers were dried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification by flash-chromatography with n-heptane/2-propanol as eluent

Vorschrift

To a mixture of trans-8-chloro-1-(4-isopropoxy-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene hydrochloride (0.070 g, 0.18 mmol) and potassium carbonate (0.073 ml, 0.53 mmol) in acetonitrile (1 ml) was added 2-(bromomethyl)pyridine hydrobromide (0.048 g, 0.18 mmol) at room temperature. Stirring for 20 h at 50° C. was followed by partitioning between 1 M aqueous sodium hydroxide solution (30 ml) and dichloromethane (30 ml). The layers were separated. The aqueous layer was extracted with two 30-ml portions of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash-chromatography with n-heptane/2-propanol as eluent gave the title compound (0.046 g, 58%) as yellow oil. MS m/e: 452 (M+H+).

Quelle