3-Chloro-1-propanol → 3-[3-(Dimethylamino)phenoxy]propan-1-ol
Reaction equation
[Na].[CH3:2][N:3]([CH3:11])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Cl[CH2:13][CH2:14][CH2:15][OH:16]>>[CH3:2][N:3]([CH3:11])[C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:13][CH2:14][CH2:15][OH:16]Participants
3
Procedure
Preparation analogously to Example 70 by the reaction of 3-dimethylaminophenol sodium salt with 3-chloro-1-propanol to give 3-(3-dimethylaminophenoxy)-1-propanol (b.p.0.7 =150°-5°; yield 57%), which is converted quantitatively into 3-(3-dimethylaminophenoxy)-propyl 1-methanesulphonate (oil) and is reacted with excess 5-amino-5-desoxy-1.4;3.6-dianhydro-L-iditol 2-nitrate in boiling ethanol. Isolation as hydrochloride. Yield, after recrystallisation from ethanol+active charcoal: 38.2%.
Workup
- customPreparation analogously to Example 70