GB728406A - Process for the preparation of 5-hydroxytryptamine and addition salts thereof - Google Patents
Process for the preparation of 5-hydroxytryptamine and addition salts thereofInfo
- Publication number
- GB728406A GB728406A GB182/53A GB18253A GB728406A GB 728406 A GB728406 A GB 728406A GB 182/53 A GB182/53 A GB 182/53A GB 18253 A GB18253 A GB 18253A GB 728406 A GB728406 A GB 728406A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tryptamine
- hydroxytryptamine
- benzyloxytryptamine
- hydrogen
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
5.-Hydroxytryptamine of the formula <FORM:0728406/IV (b)/1> or an addition salt thereof is prepared by debenzylating, by catalytic hydrogenation, a 5-benzyloxytryptamine or an addition salt thereof. The 5-benzyloxytryptamine is prepared from 5-benzyloxyindole of the formula <FORM:0728406/IV (b)/2> wherein X is a phenyl or substituted phenyl radical and Y is a phenyl or substituted phenyl, alkyl or cycloalkyl radical or hydrogen, by reaction with a Grignard reagent, reacting the resulting 5-benzyloxyindole magnesium halide with a haloacetonitrile to produce a 5-benzyloxy-3-indoleacetonitrile, and reducing the 5-benzyloxy-3-indoleacetonitrile to produce a 5-benzyloxytryptamine. The latter step may be carried out with lithium aluminium hydride, sodium and alcohol, or lithium borohydride, or by means of hydrogen in the presence of platinum catalyst. The 5-benzyloxytryptamine or its salt is debenzylated with hydrogen in the presence of a catalyst, preferably a 10 per cent palladium-charcoal catalyst, in the presence of a solvent such as an alkanol or lower ketone. The free 5-hydroxytryptamine base may be converted into an acid addition salt by adding a stoichiometric quantity of the acid to a solution of the base and adding a precipitating agent for the salt, e.g. acetone for precipitating the creatinine sulphate salt, ether for the sulphate, hydrochloride, acetate or citrate, and water for the picrate. The precipitation is usually conducted at the boiling point. In examples (1) 5-benzyloxyindole is added to a Grignard reagent prepared from magnesium and methyl iodide, followed by chloroacetonitrile, and the 5 - benzyloxy - 3 - indole - acetonitrile is reduced with lithium aluminium hydride to give 5-benzyloxytryptamine, which is then treated with hydrogen and palladium-charcoal catalyst in the presence of ethanol and the 5-hydroxytryptamine precipitated as the creatinine sulphate addition salt by means of sulphuric acid and creatinine sulphate solution; (2) 5-hydroxytryptamine is prepared by debenzylating 5-(p-methylbenzyloxy)-tryptamine by means of hydrogen as in (1); and in other examples, 5-hydroxytryptamine and its creatinine sulphate salt are similarly prepared from (3) 5-(p-benzylbenzyloxy) - tryptamine, (4) 5 - (p - methoxybenzyloxy) - tryptamine, (5) 5 - benzhydryloxytryptamine, (6) 5-(p-cyclopentylbenzyloxy)-tryptamine, (7) 5 - (p - iodobenzyloxy) - tryptamine, (8) 5 - (a - methylbenzyloxy) - tryptamine, and (9) 5 - (a - cyclohexylbenzyloxy)-tryptamine. The examples also specify a large number of alternative substituted 5-benzyloxyindoles within the general formula given above, as starting materials in the process.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US728406XA | 1952-01-04 | 1952-01-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB728406A true GB728406A (en) | 1955-04-20 |
Family
ID=22110067
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB182/53A Expired GB728406A (en) | 1952-01-04 | 1953-01-02 | Process for the preparation of 5-hydroxytryptamine and addition salts thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB728406A (en) |
-
1953
- 1953-01-02 GB GB182/53A patent/GB728406A/en not_active Expired
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