Реакция #1005982

Уравнение реакции

aminodiphenylmethane

cis-1,4-dichloro-2-butene

→

product

Выход 43.0%

1-(Benzhydryl)-3-pyrroline

Выход 43.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другое20 hours
2. 2
   ФильтрацияThe white solid was filtered
3. 3
   Промывкаwashed with dichloromethane
4. 4
   ТемператураThe 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
   ФильтрацияThe resulting white solid was filtered
8. 8
   Промывкаwashed with dichloromethane
9. 9
   Промывкаthe filtrated was washed with saturated solution of NaHCO3, water
10. 10
    Сушкаdried over Na2SO4
11. 11
    Фильтрацияfiltered
12. 12
    Концентрированиеconcentrated
13. 13
    ДругоеThe crude was purified by flash chromatography

Методика

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.

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