反应详情

86.6 g of 3-methyl 5-(3-bromopropyl) (-)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate, 50 g of 4,4-diphenylpiperidine hydrochloride and 69 g of finely milled potassium carbonate are heated together in 300 ml of dimethylformamide for 5 h at 100° C. with vigorous stirring and under a nitrogen atmosphere. After cooling, 500 ml of ethyl acetate and 1 l of water are added in succession and the mixture is stirred thoroughly. After phase separation, the organic phase is washed 4 times with water, dried over sodium sulphate and evaporated in vacuo. The residue is dissolved in 1 l of dioxane and 15.2 ml of concentrated hydrochloric acid solution (12.5 M, d=1.19) are added to the cooled solution; about 200 ml of the solvent mixture are then distilled off in vacuo. On standing at room temperature, the product crystallises spontaneously or after seeding or trituration; it is filtered off under suction after 16 h, washed with dioxane and diisopropyl ether and dried in vacuo at 80°-100° C. For purification, the product is dissolved in dichloromethane. After the addition of 800 ml of dioxane, the dichloromethane is distilled off again. The product which has crystallised out after seeding and standing at room temperature for 16 hours is filtered off under suction, washed with dioxane and diisopropyl ether and dried at 100° C. 97 g of the title compound of m.p. 158°-160° C. and [α]22 436 =-39° (c=1, methanol) or [α]22D =-14.4° (c=1. methanol) are obtained.

1. temperatureAfter cooling
2. stirringthe mixture is stirred thoroughly
3. customAfter phase separation
4. washthe organic phase is washed 4 times with water
5. dry with materialdried over sodium sulphate
6. customevaporated in vacuo
7. dissolutionThe residue is dissolved in 1 l of dioxane
8. addition15.2 ml of concentrated hydrochloric acid solution (12.5 M, d=1.19) are added to the cooled solution
9. distillationabout 200 ml of the solvent mixture are then distilled off in vacuo
10. customOn standing at room temperature
11. customthe product crystallises spontaneously
12. filtrationit is filtered off under suction after 16 h
13. washwashed with dioxane and diisopropyl ether
14. customdried in vacuo at 80°-100° C
15. customFor purification
16. dissolutionthe product is dissolved in dichloromethane
17. additionAfter the addition of 800 ml of dioxane
18. distillationthe dichloromethane is distilled off again
19. customThe product which has crystallised out after seeding
20. filtrationis filtered off under suction
21. washwashed with dioxane and diisopropyl ether
22. customdried at 100° C