Triethylamine → 7-Methoxytryptamine hydrochloride

To a stirred, cooled (0° C.) suspension of 2-methoxyphenylhydrazine hydrochloride (14.44 g, 83 mmol) in THF (600 mL) was added 4-chlorobutanal prepared as described in Example 5 (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. ##STR40##

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

ORD-Eintrag

ord-cf891f67a37247dcb40571f0c07cb1d7

Quelldatensatz

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05488053