反应详情

To a stirred, cooled (0° C.) suspension of 2-methoxyphenylhydrazine hydrochloride (14.44 g, 83 mmol.) in THF (600 mL) was added 4-chlorobutanal (9.0 g, 84 mmol.) followed by dropwise addition of triethylamine (8.6 g, 85 mmol.) in THF (20 mL). Upon complete addition, the cooling bath was removed and the solution stirred for 1 hour. The reaction mixture was filtered and the filter cake washed with THF (100 mL). The combined filtrates were concentrated to an orange oil, which was dissolved in methanol (150 mL) and water (5 mL). The solution was transferred to a sealable tube and purged with nitrogen for 10 minutes. The tube was sealed and placed in an oilbath preheated to 95° C. After heating for 14 hours, the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was partitioned between saturated aqueous potassium carbonate and 3:1 chloroform: 2-propanol. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (15% methanol, 0.2% NH4OH, in chloroform as eluent). The fractions containing product were pooled and concentrated under reduced pressure. The residue was dissolved in methanol and treated with dry HCl and concentrated to afford 7-methoxytryptamine hydrochloride (4.04 g) as a stable foam, which was used without further purification. ##STR30##

1. temperatureTo a stirred, cooled
2. additionUpon complete addition
3. customthe cooling bath was removed
4. filtrationThe reaction mixture was filtered
5. washthe filter cake washed with THF (100 mL)
6. concentrationThe combined filtrates were concentrated to an orange oil, which
7. dissolutionwas dissolved in methanol (150 mL)
8. customThe solution was transferred to a sealable tube
9. custompurged with nitrogen for 10 minutes
10. customThe tube was sealed
11. custompreheated to 95° C
12. temperatureAfter heating for 14 hours
13. concentrationconcentrated under reduced pressure
14. customThe residue was partitioned between saturated aqueous potassium carbonate and 3:1 chloroform
15. dry with materialThe organic phase was dried over sodium sulfate
16. concentrationconcentrated
17. customThe residue was purified by flash chromatography on silica gel (15% methanol, 0.2% NH4OH, in chloroform as eluent)
18. additionThe fractions containing product
19. concentrationconcentrated under reduced pressure
20. dissolutionThe residue was dissolved in methanol
21. additiontreated with dry HCl
22. concentrationconcentrated