Reaktion #62930

Reaktionsgleichung

hydrochloric acid

sodium borohydride

4,5-dihydrothiazolo[5,4-f]quinolin-2-amine

1-iodopropane

→

(±)-4,5,5a,6,7,8-hexahydro-6-propylthiazolo-[5,4-f]quinolin-2-amine

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent is removed in-vacuo
2. 2
   workup.DISSOLUTIONthe 2-amino-4,5-dihydrothiazolo[5,4-f]quinolinium iodide which remains is dissolved in 200 ml methanol
3. 3
   Sonstigethe volatile components are removed in-vacuo
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   TrocknenThe organic layer is dried over magnesium sulfate
6. 6
   Sonstigeevaporated
7. 7
   Sonstigethe residue is chromatographed

Vorschrift

The free base of 4,5-dihydrothiazolo[5,4-f]quinolin-2-amine, 5.0 g (20 mmol), is refluxed in 250 ml ethanol with 6.8 g (40 mmol) of 1-iodopropane for 20 hours. The solvent is removed in-vacuo and the 2-amino-4,5-dihydrothiazolo[5,4-f]quinolinium iodide which remains is dissolved in 200 ml methanol and treated with 1.7 g (50 mmol) of sodium borohydride in small portions, at 0° C. After 1 hour, 50 ml of 10% hydrochloric acid is added dropwise and the volatile components are removed in-vacuo. The residue is made basic with ammonium hydroxide and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, evaporated and the residue is chromatographed to yield (±)-4,5,5a,6,7,8-hexahydro-6-propylthiazolo-[5,4-f]quinolin-2-amine.

Quelle