Reacción #7914

Ecuación de reacción

potassium thiocyanate

chloride

Dimethylpyrrolidin-3-yl-amine

→

3-dimethylamino-pyrrolidine-1-carbothioic acid amide

Rendimiento 23.9%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   workup.STIRRINGAfter stirring at room temperature overnight
3. 3
   Concentraciónthe reaction was concentrated
4. 4
   workup.ADDITIONconcentrated hydrochloric acid (10 mL) was added
5. 5
   TemperaturaThe reaction was heated to 95° C.
6. 6
   workup.STIRRINGwith stirring for 1 h
7. 7
   Temperaturato cool to room temperature
8. 8
   Extracciónwas extracted with dichloromethane
9. 9
   ExtracciónThe basic solution was extracted with dichloromethane
10. 10
    Lavadowashed with brine
11. 11
    Secadodried with anhydrous sodium sulfate
12. 12
    Filtraciónfiltered
13. 13
    Concentraciónconcentrated
14. 14
    workup.ADDITIONThe mixture was diluted with diethyl ether
15. 15
    Filtraciónfiltered

Procedimiento

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.

Fuente