Reaktion #515699

Reaktionsgleichung

8-(4-benzyl-piperazin-1-yl)quinoline

vinyl chloroformate

→

yellow oil

Ausbeute 100.2%

8-(Piperazin-1-yl)-quinoline

Ausbeute 100.2%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 2 hours
2. 2
   Einengenconcentrated under vacuum
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 12 N hydrochloric acid (20 ml)
4. 4
   EinengenThe mixture was concentrated
5. 5
   Temperaturheated up to 50° C. for 2 hours
6. 6
   SonstigeThe solvent was removed under vacuum
7. 7
   workup.DISSOLUTIONthe residue was dissolved in 1 N sodium hydroxide-ethyl acetate
8. 8
   Extraktionextracted with ethyl acetate
9. 9
   Waschenwashed with water
10. 10
    TrocknenThe organic layer was dried over anhydrous sodium sulfate
11. 11
    SonstigeThe solvent was removed under vacuum

Vorschrift

To a solution of 8-(4-benzyl-piperazin-1-yl)quinoline (2.63 g, 8.7 mmol) in methylene chloride (30 ml) was added vinyl chloroformate (1.1 ml, 13 mmol) at room temperature slowly. The reaction mixture was refluxed for 2 hours, and then concentrated under vacuum. The residue was dissolved in 12 N hydrochloric acid (20 ml) and stirred at room temperature for 1 hour. The mixture was concentrated, the residue was taken up with 40 ml ethanol and heated up to 50° C. for 2 hours. The solvent was removed under vacuum, the residue was dissolved in 1 N sodium hydroxide-ethyl acetate and extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under vacuum. Chromatography (10-30% methanol -methylene chloride plus ammonium hydroxide) afforded 1.86 g (90%) yellow oil; MS EI m/e 213 (M)+.

Quelle