Reacción #4460

Ecuación de reacción

N-(phenylcarbamoylimino)pyridinium

sodium borohydride

hydrochloric acid

→

N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine

Disolventes

ethanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated to a volume of ca. 15 ml
2. 2
   OtroThe crystalline precipitate was collected
3. 3
   Lavadowashed with water
4. 4
   Otrodried in vacuo
5. 5
   workup.DISSOLUTIONThe crude product was dissolved in ethyl acetate
6. 6
   Extracciónextracted with 10% hydrochloric acid (20 ml)
7. 7
   Extracciónextracted with ethyl acetate (30 ml)
8. 8
   LavadoThe organic layer was washed with aqueous sodium bicarbonate (10 ml)
9. 9
   Secadodried over magnesium sulfate
10. 10
    Otroevaporated

Procedimiento

To a solution of N-(phenylcarbamoylimino)pyridinium ylide (0.64 g) in a mixture of ethanol (30 ml) and water (10 ml) was added sodium borohydride (0.20 g) at ambient temperature. After being stirred for 4 hours, the reaction mixture was acidified with 1N hydrochloric acid, concentrated to a volume of ca. 15 ml. The crystalline precipitate was collected, washed with water and dried in vacuo. The crude product was dissolved in ethyl acetate and extracted with 10% hydrochloric acid (20 ml). The extract was adjusted to pH 3 with aqueous sodium bicarbonate and extracted with ethyl acetate (30 ml). The organic layer was washed with aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate and evaporated to give N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine (0.28 g), which was recrystallized from ethyl acetate to afford colorless needles (0.15 g). mp: 157°-159° C.

Fuente