4-Amino-1-butanol → 4-(N-(3,5-Dimethylphenyl)amino)butanol

HRID 1243100Notes

Reaction equation

HRID 1243100 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]>>[CH3:8][C:6]1[CH:7]=[C:2]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:3]=[C:4]([CH3:9])[CH:5]=1

Participants

3

Reactant 2

HCID 258684-Amino-1-butanolHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 219407104-(N-(3,5-Dimethylphenyl)amino)butanolYield 90%

Procedure

Using the general procedure, 5-bromo-m-xylene (136 μL, 1.0 mmol) was coupled with 4-aminobutanol (138 μL, 1.5 mmol). Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (2:1) as eluent afforded the desired product as a colorless oil (174 mg, 90% yield). Rf=0.4 (hexane/ethyl acetate=1:1).

Workup

  1. customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record
ord-4f27694ed7b14945a841be8531b91eaf
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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