反应详情

A chilled solution (-4° C.) of 126 g of 2,2-dimethyl-N-[(2-methyl)phenyl]propanamide in 900 ml of tetrahydrofuran was treated dropwise over 1.5 hr with n-butyl lithium (500 ml of a 2.5M solution in hexanes). After the addition was complete, the resulting solution was stirred for 1 hr, with cooling, and was then treated over 0.5 hr with a solution of 91.77 g of 2-methylbenzaldehyde methyl imine. The reaction mixture was quenched by rapid addition of water. After concentration the residue was extracted with dichloromethane. The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated. A 50 g portion of the residue (213 g) was acidified with 10% hydrochloric acid and partitioned with toluene. The aqueous layer was basified with a 50% sodium hydroxide solution and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated. Upon standing under nitrogen overnight in a refrigerator a solid formed, which was triturated with hexane to give 2,2-dimethyl-N-[2 -[2-methylamino-2-(2-methylphenyl)ethyl]phenyl]propanamide, mp 77°-79° C.

1. additionAfter the addition
2. temperaturewith cooling
3. customThe reaction mixture was quenched by rapid addition of water
4. concentrationAfter concentration the residue
5. extractionwas extracted with dichloromethane
6. extractionThe combined organic extract
7. dry with materialwas dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. custompartitioned with toluene
11. extractionextracted with dichloromethane
12. dry with materialThe organic layer was dried over anhydrous sodium sulfate
13. concentrationconcentrated
14. waitUpon standing under nitrogen overnight in a refrigerator
15. customa solid formed
16. customwhich was triturated with hexane