反应详情

5 cc of methylmercaptan is added to a solution of methyl 2-formylbenzoate (3.6 g) and 3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)-1-aminopropane (9.6 g)in tetrahydrofuran (255 cc) in an autoclave, at a temperature close to -20° C. in the course of 5 minutes. The solution is heated to a temperature close to 60° C. for 4 hours. After cooling to a temperature close to 20° C., the solution is poured into 1N sodium hydroxide (300 cc) and washed with distilled water (3×500 cc). The organic extract is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue obtained is dissolved in ethyl acetate (20 cc) and poured onto silica (750 g) contained in a column of 8 cm diameter. Elution is carried out with ethyl acetate. The first 3400 cc are eliminated and the next 3100 cc are evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue obtained is dissolved in methyl ethyl ketone (70 cc). A solution of oxalic acid (1.7 g) in methyl ethyl ketone (20 cc) is added and agitation continued for 1 hour at a temperature close to 20° C. The precipitate formed is separated by filtration. 5.9 g of 3-methylthio-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone oxalate are thus obtained, melting at 169° C.

1. customclose to -20° C. in the course of 5 minutes
2. temperatureThe solution is heated to a temperature
3. customclose to 60° C. for 4 hours
4. temperatureAfter cooling to a temperature
5. customclose to 20° C.
6. washwashed with distilled water (3×500 cc)
7. extractionThe organic extract
8. dry with materialis dried over anhydrous magnesium sulphate
9. filtrationfiltered
10. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
11. customThe residue obtained
12. additionpoured onto silica (750 g)
13. washElution
14. customthe next 3100 cc are evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
15. customThe residue obtained
16. customclose to 20° C
17. customThe precipitate formed
18. customis separated by filtration