Reaction #1005982

Reaction equation

aminodiphenylmethane

cis-1,4-dichloro-2-butene

→

product

Yield 43.0%

1-(Benzhydryl)-3-pyrroline

Yield 43.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Other20 hours
2. 2
   FiltrationThe white solid was filtered
3. 3
   Washwashed with dichloromethane
4. 4
   TemperatureThe 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
   Washwashed with dichloromethane
9. 9
   Washthe filtrated was washed with saturated solution of NaHCO3, water
10. 10
    Dryingdried over Na2SO4
11. 11
    Filtrationfiltered
12. 12
    Concentrationconcentrated
13. 13
    OtherThe crude was purified by flash chromatography

Procedure

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