反应详情

2.5 g of 2-acetylbenzoic acid is added to a solution of 3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)-1-aminopropane (7.8 g) in acetonitrile (90 cc) at a temperature close to 20° C. in the course of 10 minutes. Agitation is continued for 4 hours then 7.6 g of 3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)-1-aminopropane hydrochloride is added in the course of 30 minutes. Then 1.2 g of sodium cyanoborohydride is added to the suspension obtained, in the course of 5 minutes. Agitation is continued for 16 hours. The suspension is filtered and the precipitate washed with acetonitrile (20 cc). The organic extracts are combined, diluted with methylene chloride (200 cc) then washed with distilled water (120 cc), dried over anhydrous magnesium sulphate, treated with animal charcoal, filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue obtained is poured onto alumina (750 g) contained in a column of 6 cm diameter. Elution is carried out with ethyl acetate (1000 cc) and the corresponding eluates are eliminated. Then elution is carried out with a mixture of ethyl acetate and methanol (98-2 by volume) (1000 cc) and the corresponding eluates are evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C. The residue obtained is dissolved in methyl ethyl ketone (20 cc). A solution of oxalic acid (0.3 g) in methyl ethyl ketone (10 cc) is added and agitation continued for 1 hour at a temperature close to 20° C. The precipitate formed is separated by filtration and recrystallized from boiling acetonitrile (80 cc). 0.9.g of 3-methyl-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone oxalate are thus obtained, melting at 147° C.

1. customclose to 20° C. in the course of 10 minutes
2. customobtained, in the course of 5 minutes
3. waitAgitation is continued for 16 hours
4. filtrationThe suspension is filtered
5. washthe precipitate washed with acetonitrile (20 cc)
6. additiondiluted with methylene chloride (200 cc)
7. washthen washed with distilled water (120 cc)
8. dry with materialdried over anhydrous magnesium sulphate
9. additiontreated with animal charcoal
10. filtrationfiltered
11. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
12. customThe residue obtained
13. additionis poured onto alumina (750 g)
14. washElution
15. washThen elution
16. additionis carried out with a mixture of ethyl acetate and methanol (98-2 by volume) (1000 cc)
17. customthe corresponding eluates are evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C
18. customThe residue obtained
19. waitagitation continued for 1 hour at a temperature
20. customclose to 20° C
21. customThe precipitate formed
22. customis separated by filtration
23. customrecrystallized