GB813777A - 2-(ª -amino-ethyl)-5-hydroxy-indole and a process for the preparation thereof - Google Patents

2-(ª -amino-ethyl)-5-hydroxy-indole and a process for the preparation thereof

Info

Publication number
GB813777A
GB813777A GB13970/57D GB1397057D GB813777A GB 813777 A GB813777 A GB 813777A GB 13970/57 D GB13970/57 D GB 13970/57D GB 1397057 D GB1397057 D GB 1397057D GB 813777 A GB813777 A GB 813777A
Authority
GB
United Kingdom
Prior art keywords
indole
amino
ethyl
hydroxy
benzyloxy
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
Application number
GB13970/57D
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
National Starch and Chemical Investment Holding Corp
Original Assignee
JR Geigy AG
National Starch and Chemical Investment Holding Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by JR Geigy AG, National Starch and Chemical Investment Holding Corp filed Critical JR Geigy AG
Publication of GB813777A publication Critical patent/GB813777A/en
Expired legal-status Critical Current

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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

The invention comprises 2-(b -amino-ethyl)-5-hydroxy-indole having the formula <FORM:0813777/IV (b)/1> salts thereof with mineral acids, the double salt of 2-(b -amino-ethyl)-5-hydroxy-indole with one mol. each of creatinine, sulphuric acid and water, and a process for the preparation of 2-(b -amino - ethyl) - 5 - hydroxy - indole which comprises reducing a 5-benzyloxyindole - 2 - carboxylic acid dialkylamide with an alkali metalearth metal hydride to form a 2-dialkylaminomethyl-5-benzyloxyindole, quaternizing this indole with a lower molecular alkyl halide or dialkyl sulphate, reacting the 2-trialkyl-ammoniomethyl - 5 - benzyloxyindole halide or alkyl sulphate obtained with an alkali metal cyanide, either hydrogenating the 5-benzyloxy-indolyl-2-acetonitrile to the 2-(b -amino-ethyl)-5-benzyloxy indole or reducing it with an alkali metalearth metal hydride, and converting the amino compound by hydrogenolysis with catalytically activated hydrogen into the 2-(b -amino-ethyl)-5-hydroxy-indole. The dialkylamide may be obtained by reacting the carboxylic acid chloride with dimethylamine, and may be reduced with lithium aluminium hydride. The 5-benzyloxy-2-dialkylaminomethylindole thus obtained may be quaternized with methyl iodide and reacted with sodium or potassium cyanide. The hydrogenolysis may be effected in alcoholic solution by hydrogen at room temperature in the presence of palladium charcoal. Using hydrogen and a Raney nickel catalyst 5-benzyloxy indolyl - (2) - acetonitrile may be converted directly to the desired 2-(b -amino-ethyl)-5-hydroxy-indole. The product forms salts with mineral acids and a double salt with 1 mol. each of creatinine, sulphuric acid and water. The process is illustrated by an example.
GB13970/57D 1956-05-05 1957-05-02 2-(ª -amino-ethyl)-5-hydroxy-indole and a process for the preparation thereof Expired GB813777A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH813777X 1956-05-05

Publications (1)

Publication Number Publication Date
GB813777A true GB813777A (en) 1959-05-21

Family

ID=4538760

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13970/57D Expired GB813777A (en) 1956-05-05 1957-05-02 2-(ª -amino-ethyl)-5-hydroxy-indole and a process for the preparation thereof

Country Status (1)

Country Link
GB (1) GB813777A (en)

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