HCID 14871689, compound → 3-(1-Dimethylaminoethyl)phenol

94 g of [1-(3-methoxyphenyl)ethyl]dimethylamine (V) are dissolved in 285 ml of azeotropic hydrobromic acid and the resulting solution is refluxed under stirring using a reflux condenser for 12 hours (bath temperature 145-150° C.). During boiling, the reaction mixture darkens. The solution is then left to cool down to room temperature. Excess hydrobromic acid is evaporated using a rotary vacuum evaporator and the evaporation residue is dissolved in 200 ml of water. The solution is extracted with 3×100 ml ethylacetate. The aqueous fraction is then gradually alkalized with the saturated solution of sodium carbonate with constant stirring (foam creation). The solution becomes milky turbid and it is extracted with 3×200 ml ethylacetate. The ethylacetate fraction is shaken out 1× with water, 1× with brine and dried with anhydrous magnesium sulfate. Activated carbon is added before filtering off the desiccant and the desiccant along with the carbon are filtered off. The ethylacetate solution of compound (IV) is used for the next step.

1. temperaturethe resulting solution is refluxed
2. customfor 12 hours
3. custom(bath temperature 145-150° C.)
4. waitThe solution is then left
5. customExcess hydrobromic acid is evaporated
6. customa rotary vacuum evaporator
7. dissolutionthe evaporation residue is dissolved in 200 ml of water
8. extractionThe solution is extracted with 3×100 ml ethylacetate
9. stirringwith constant stirring (foam creation)
10. extractionis extracted with 3×200 ml ethylacetate
11. stirringThe ethylacetate fraction is shaken out 1× with water, 1× with brine
12. dry with materialdried with anhydrous magnesium sulfate
13. additionActivated carbon is added
14. filtrationbefore filtering off the desiccant and the desiccant along with the carbon
15. filtrationare filtered off

ORD record

ord-cc8c3a6220ca42c881043a474334a25b

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544840B2