Reacción #1005982

Ecuación de reacción

aminodiphenylmethane

cis-1,4-dichloro-2-butene

→

product

Rendimiento 43.0%

1-(Benzhydryl)-3-pyrroline

Rendimiento 43.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro20 hours
2. 2
   FiltraciónThe white solid was filtered
3. 3
   Lavadowashed with dichloromethane
4. 4
   TemperaturaThe filtrated was cooled at 0° C.
5. 5
   workup.ADDITIONHCl 37% (2.5 ml) was added carefully
6. 6
   workup.STIRRINGthe suspension was stirred overnight
7. 7
   FiltraciónThe resulting white solid was filtered
8. 8
   Lavadowashed with dichloromethane
9. 9
   Lavadothe filtrated was washed with saturated solution of NaHCO3, water
10. 10
    Secadodried over Na2SO4
11. 11
    Filtraciónfiltered
12. 12
    Concentraciónconcentrated
13. 13
    OtroThe crude was purified by flash chromatography

Procedimiento

To a solution of aminodiphenylmethane (9.70 g, 51.46 mmol) in dichloromethane (6 ml) was added cis-1,4-dichloro-2-butene (1.18 g, 9.02 mmol). The mixture was stirred at r.t. 20 hours. The white solid was filtered and washed with dichloromethane. The filtrated was cooled at 0° C. and HCl 37% (2.5 ml) was added carefully and the suspension was stirred overnight. The resulting white solid was filtered and washed with dichloromethane and the filtrated was washed with saturated solution of NaHCO3, water, dried over Na2SO4, filtered and concentrated. The crude was purified by flash chromatography: silica gel, gradient dichloromethane to dichloromethane:methanol 4% to afforded the product (0.90 g, 43%) as white solid. M.p. 90-91° C.

Fuente