反応 #815999

反応方程式

N-benzyl-2-chloroethylamine hydrochloride

sodium hydride

4-(1H-imidazol-yl)phenol

H2O

→

title compound

2-[4-(1H-Imidazol-1-yl)phenoxy]-N-(phenylmethyl)ethanamine dihydrochloride

溶媒

DMF

反応条件

後処理

1. 1
   温度Chill the reaction mixture on an ice/MeOH bath
2. 2
   workup.ADDITIONduring the addition
3. 3
   workup.ADDITIONAfter addition
4. 4
   workup.ADDITIONAfter addition
5. 5
   温度heat the stirring suspension to 65° C
6. 6
   その他progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol, 9:1)
7. 7
   その他At the completion of the reaction
8. 8
   温度cool to room temperature
9. 9
   その他Remove
10. 10
    ろ過the solidsby suction filtration
11. 11
    その他evaporate the solvents

実験手順

To a suspension of 39.5 g (0.82 mol) sodium hydride in 500 mL DMF add 37.3 g (0.233 mol) 4-(1H-imidazol-yl)phenol portionwise. Chill the reaction mixture on an ice/MeOH bath during the addition. After addition, stir the reaction mixture at room temperature until gas evolution ceases. After this time, return the reaction mixture to the ice bath and add 50.2 g (0.29 g) N-benzyl-2-chloroethylamine hydrochloride portionwise. After addition is complete, heat the stirring suspension to 65° C. Followthe progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol, 9:1). At the completion of the reaction, cool to room temperature and slowly add 20 mL H2O. Remove the solidsby suction filtration and evaporate the solvents. Chromatograph the resulting oil on silica gel using (CH2Cl2 :MeOH, 98:2), to isolate the title compound as the free base. Dissolve the free base in excess 3 M methanolic HCl and evaporate the solvents to give the title compound.

出典