تفاعل #572857

معادلة التفاعل

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

المذيبات

ether

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر