3-Chloro-1-propanol → 3-[3-(Dimethylamino)phenoxy]propan-1-ol

HRID 1902495Notes

Reaction equation

HRID 1902495 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

Reactant 2

HCID 123133-Chloro-1-propanolHCID 70552614HCID 70552614, compound

Product 1

HCID 30190163-[3-(Dimethylamino)phenoxy]propan-1-olYield 57%

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

  1. customPreparation analogously to Example 70

Sources & evidence

ORD record
ord-655fb93409cf4be0bb500d063963267a
Source dataset
uspto-grants-1982_12
Patent number
US04363805

Reaction notes

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