Reaktion #7914

Reaktionsgleichung

potassium thiocyanate

chloride

Dimethylpyrrolidin-3-yl-amine

→

3-dimethylamino-pyrrolidine-1-carbothioic acid amide

Ausbeute 23.9%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   workup.STIRRINGAfter stirring at room temperature overnight
3. 3
   Einengenthe reaction was concentrated
4. 4
   workup.ADDITIONconcentrated hydrochloric acid (10 mL) was added
5. 5
   TemperaturThe reaction was heated to 95° C.
6. 6
   workup.STIRRINGwith stirring for 1 h
7. 7
   Temperaturto cool to room temperature
8. 8
   Extraktionwas extracted with dichloromethane
9. 9
   ExtraktionThe basic solution was extracted with dichloromethane
10. 10
    Waschenwashed with brine
11. 11
    Trocknendried with anhydrous sodium sulfate
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated
14. 14
    workup.ADDITIONThe mixture was diluted with diethyl ether
15. 15
    Filtrationfiltered

Vorschrift

To a suspension of potassium thiocyanate (2.02 g, 20.8 mmol) in acetone (10.7 mL) at 0° C. was slowly added pivolyl chloride (2.6 mL, 21.1 mmol). The mixture was stirred at 0° C. for 3 h. Dimethylpyrrolidin-3-yl-amine (2.44 g, 21.3 mmol) was added slowly at 0° C., and the reaction was allowed to warm to room temperature. After stirring at room temperature overnight, the reaction was concentrated, and concentrated hydrochloric acid (10 mL) was added. The reaction was heated to 95° C. with stirring for 1 h. The mixture was allowed to cool to room temperature, and was extracted with dichloromethane. The aqueous layer was made basic with 20% aqueous sodium hydroxide. The basic solution was extracted with dichloromethane. The organics were combined, washed with brine, dried with anhydrous sodium sulfate, filtered, and concentrated. The mixture was diluted with diethyl ether and filtered to provide pure 3-dimethylamino-pyrrolidine-1-carbothioic acid amide (135) (0.863 g, 23.3%) as a white solid.

Quelle