Reaktion #572857

Reaktionsgleichung

trans-(±)-2-bromo-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline

pyrrolidine

maleic acid

→

trans-(±)-2-(1-pyrrolidinyl)-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline maleate

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA reaction mixture, prepared from 6.6 g
2. 2
   Temperaturto reflux temperature for about 18 hours
3. 3
   Temperaturwas then cooled
4. 4
   SonstigeThe volatile constituents were removed in vacuo
5. 5
   workup.ADDITIONthe resulting residue diluted with water
6. 6
   ExtraktionThe alkaline layer was extracted several times with equal volumes of chloroform
7. 7
   Waschenthe combined extracts washed with water and with saturated aqueous sodium chloride
8. 8
   Sonstigewere then dried
9. 9
   SonstigeThe solvent was evaporated
10. 10
    workup.DISSOLUTIONThe residue was therefore dissolved in chloroform
11. 11
    Sonstigethe chloroform solution chromatographed over a florisil column
12. 12
    SonstigeSeventeen hundredths grams of a light yellow glass were obtained by this procedure
13. 13
    SonstigeA solid maleate salt precipitated
14. 14
    SonstigeThe ether was removed by decantation
15. 15
    Sonstigethe solid salt recrystallized from a mixture of ethanol and ether

Vorschrift

A reaction mixture, prepared from 6.6 g. of trans-(±)-2-bromo-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline and 20 ml. of pyrrolidine, was heated to reflux temperature for about 18 hours and was then cooled. The volatile constituents were removed in vacuo and the resulting residue diluted with water. The aqueous mixture was made strongly basic with concentrated aqueous ammonium hydroxide. The alkaline layer was extracted several times with equal volumes of chloroform. The chloroform extracts were combined, and the combined extracts washed with water and with saturated aqueous sodium chloride and were then dried. The solvent was evaporated therefrom in vacuo. TLC (9:1 CHCl3 /MeOH+a trace of aqueous ammonium hydroxide) showed one spot, more polar than starting material. The residue was therefore dissolved in chloroform and the chloroform solution chromatographed over a florisil column using chloroform as the eluant. Seventeen hundredths grams of a light yellow glass were obtained by this procedure. The glass was dissolved in ether and 0.06 g. of maleic acid in ethereal solution added thereto. A solid maleate salt precipitated. The ether was removed by decantation and the solid salt recrystallized from a mixture of ethanol and ether. Five hundredths grams of trans-(±)-2-(1-pyrrolidinyl)-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline maleate were obtained melting with decomposition at 184° C.

Quelle