反应详情

A solution of 2-(N,N-dimethylaminomethyl)phenol (10.0 g, which contains 30% phenol by weight) in DMF (10 ml) was added dropwise with stirring to a suspension of sodium hydride (3.14 g, 60% dispersion in mineral oil) in DMF (75 ml) at ambient temperature under nitrogen. After the addition the mixture was stirred at ambient temperature for 30 minutes. A solution of 2-chloro-N,N-diethylethylamine in toluene (70 ml) [prepared by dissolving the hydrochloride (14.8 g) in water (20 ml), adding aqueous sodium hydroxide (5M) to basify the mixture and then extracting the mixture with toluene 3×20 ml, drying, filtering and then making up to 70 ml as required] was added dropwise over a period of 2 minutes and the resulting mixture heated on a steam bath for 18 hours under nitrogen. The mixture was poured into ice/water (500 ml) and sodium hydroxide solution was added until the mixture was basic (pH=14). The mixture was extracted with ether to give a residue which was distilled under vacuum. The highest boiling fraction (b.p. 105°-110° C. at 0.6 mbar) was dissolved in ether and acidified with ethereal hydrogen chloride. The solvent was removed under reduced pressure. The residue was dissolved in propan-2-ol and ether added to induce precipitation. The solid was collected by filtration and recrystallised from propan-2-ol to give 2-(2-diethylaminoethoxy)-N,N-dimethylbenzylamine dihydrochloride, m.p. 213°-214° C.

1. additionAfter the addition the mixture
2. extractionextracting the mixture with toluene 3×20 ml
3. customdrying
4. filtrationfiltering
5. additionwas added dropwise over a period of 2 minutes
6. temperaturethe resulting mixture heated on a steam bath for 18 hours under nitrogen
7. additionThe mixture was poured into ice/water (500 ml) and sodium hydroxide solution
8. additionwas added until the mixture
9. extractionThe mixture was extracted with ether
10. customto give a residue which
11. distillationwas distilled under vacuum
12. dissolutionThe highest boiling fraction (b.p. 105°-110° C. at 0.6 mbar) was dissolved in ether
13. customThe solvent was removed under reduced pressure
14. dissolutionThe residue was dissolved in propan-2-ol
15. additionether added
16. customprecipitation
17. filtrationThe solid was collected by filtration
18. customrecrystallised from propan-2-ol