反応 #1005982

反応方程式

aminodiphenylmethane

cis-1,4-dichloro-2-butene

→

product

収率 43.0%

1-(Benzhydryl)-3-pyrroline

収率 43.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他20 hours
2. 2
   ろ過The white solid was filtered
3. 3
   洗浄washed with dichloromethane
4. 4
   温度The 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
   ろ過The resulting white solid was filtered
8. 8
   洗浄washed with dichloromethane
9. 9
   洗浄the filtrated was washed with saturated solution of NaHCO3, water
10. 10
    乾燥dried over Na2SO4
11. 11
    ろ過filtered
12. 12
    濃縮concentrated
13. 13
    その他The crude was purified by flash chromatography

実験手順

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.

出典