Reaktion #1005982

Reaktionsgleichung

aminodiphenylmethane

cis-1,4-dichloro-2-butene

→

product

Ausbeute 43.0%

1-(Benzhydryl)-3-pyrroline

Ausbeute 43.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige20 hours
2. 2
   FiltrationThe white solid was filtered
3. 3
   Waschenwashed with dichloromethane
4. 4
   TemperaturThe 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
   Waschenwashed with dichloromethane
9. 9
   Waschenthe filtrated was washed with saturated solution of NaHCO3, water
10. 10
    Trocknendried over Na2SO4
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated
13. 13
    SonstigeThe crude was purified by flash chromatography

Vorschrift

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.

Quelle