反应详情

温度

5 °C

To a flask equipped with a stirrer, dropping funnel, condenser and gas inlet tube maintained under a nitrogen atmosphere there is added at room temperature 40.0 g. (0.28 mole) of o-methyl-N-methyl benzamide and 250 ml. of anhydrous tetrahydrofuran. The reaction flask is immersed in an ice bath and cooled to an internal temperature of 5° C. Stirring is initiated and 360 ml. of 1.6 M. n-butyllithium (0.616 mole) in hexane is added dropwise for about 1 hour maintaining the temperature below 8° C. The resulting red dilithio salt (compound VIII) is stirred at 5° C. for 1 additional hour and the reaction flask is then immersed in a dry-ice acetone bath and cooled to an internal temperature of -30° C. To the cold reaction mixture a solution of 49.7 g. (0.28 mole) 3-dimethylaminopropiophenone in 140 ml. anhydrous tetrahydrofuran is added dropwise in ca. 45 minutes maintaining the temperature between -30° C. and -20° C. The resulting reaction mixture is stirred at -25° C. for 1 hour, allowed to warm to -10° C. in ca. 1 hour, and then treated with 200 ml. of saturated aqueous ammonium chloride while maintaining the temperature below 0° C. The resulting solid is filtered, washed thoroughly with water and recrystallized from methylene chloride-ether (1:1) to give 2-(β-[2-dimethylaminoethyl]-β-hydroxyphenethyl)-N-methylbenzamide; m.p. 139.5 to 140.5° C.

1. customTo a flask equipped with a stirrer
2. temperaturemaintained under a nitrogen atmosphere
3. additionthere is added at room temperature 40.0 g
4. customThe reaction flask is immersed in an ice bath
5. temperaturemaintaining the temperature below 8° C
6. customthe reaction flask is then immersed in a dry-ice acetone bath
7. temperaturecooled to an internal temperature of -30° C
8. customTo the cold reaction mixture a solution of 49.7 g
9. temperaturemaintaining the temperature between -30° C. and -20° C
10. customThe resulting reaction mixture
11. stirringis stirred at -25° C. for 1 hour
12. temperatureto warm to -10° C. in ca. 1 hour
13. additiontreated with 200 ml
14. filtrationThe resulting solid is filtered
15. washwashed thoroughly with water
16. customrecrystallized from methylene chloride-ether (1:1)