Method of production of essentially pure melatonin and the metho

Details Method of production of essentially pure melatonin and the metho Method of production of essentially pure melatonin and the metho

1994-06-02

1997-10-14

Grumbling, Matthew V.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514 46, 536 276, 548504, 548507, C07D20916, C07D47334, A61K 3140, A61K 3152

Patent

active

RE0356310

ABSTRACT:
A method of synthesizing an indole derivative of the tryptamine type steps of 1) reacting potassium phthalimide and 1,3-di-bromopropane to obtain 3-bromopropylphthalimide; 2) reacting 3-bromopropylphthalimide with sodium acetoacetic ester in ethanol to obtain ethyl-2-acetyl-5-phthalimidopentanoate; 3) reacting the product from step 2) with diazo-p-anisidine to obtain 2-carboxyethyl-3-(2-phthalimidoethyl)-5-methoxy-indole; 4) reacting the 2-carboxyethyl-3-(2-phthalimidoethyl)-5-methoxy-indole with 2N/NaOH and then 20% H.sub.2 SO.sub.4 to obtain impure 5-methoxytriptamine, which is purified by means of hexamethyldisilazane. The mono and disubstituted derivatives are obtained and the monosubstituted derivative is hydrolyzed with aqueous methanol and then recrystallized from ethanol. The N-acetyl Melatonin of high purity is obtained for prophylaxy and also against AIDS (Acquired Immuno Deficiency Syndrome).

REFERENCES:
patent: 2248155 (1941-06-01), Zellner
patent: 2416258 (1947-02-01), Jenkins et al.
patent: 3947584 (1976-03-01), Zirngibl et al.
Kirk-Othmer, "Encyclopedia of Chemical Technology, 2nd ed., " vol. 4 (1964), pp. 149-153.
Fessenden and Fessenden, "Organic Chemistry" (1982) pp. 624, 670-672, 714-716.
Robert L. Grob, ed. "Modern Practices of Gas Chromatography" (1977) pp. 611-613.
Katritzky, ed. "Comprehensive Heterocyclic Chemistry" (1984) pp. 334-338.
Houlihan, ed. "Indoles, Part Three," (1979) pp. 12-20.

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