Réaction #1005982

Équation de réaction

aminodiphenylmethane

cis-1,4-dichloro-2-butene

→

product

Rendement 43.0%

1-(Benzhydryl)-3-pyrroline

Rendement 43.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autre20 hours
2. 2
   FiltrationThe white solid was filtered
3. 3
   Lavagewashed with dichloromethane
4. 4
   TempératureThe 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
   FiltrationThe resulting white solid was filtered
8. 8
   Lavagewashed with dichloromethane
9. 9
   Lavagethe filtrated was washed with saturated solution of NaHCO3, water
10. 10
    Séchagedried over Na2SO4
11. 11
    Filtrationfiltered
12. 12
    Concentrationconcentrated
13. 13
    AutreThe crude was purified by flash chromatography

Mode opératoire

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.

Source