GB773440A - 5-chloro- or bromo-2-methyl-3-(n-substituted-amino-methyl)-indoles and process for their preparation - Google Patents

5-chloro- or bromo-2-methyl-3-(n-substituted-amino-methyl)-indoles and process for their preparation

Info

Publication number
GB773440A
GB773440A GB19115/55A GB1911555A GB773440A GB 773440 A GB773440 A GB 773440A GB 19115/55 A GB19115/55 A GB 19115/55A GB 1911555 A GB1911555 A GB 1911555A GB 773440 A GB773440 A GB 773440A
Authority
GB
United Kingdom
Prior art keywords
methyl
chloro
bromo
preparation
indoles
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
GB19115/55A
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.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
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 Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Publication of GB773440A publication Critical patent/GB773440A/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

Abstract

The invention comprises 5-chloro- and 5-bromo - 2 - methyl - 3 - (N - substituted - amino - methyl)-indoles of the general formula <FORM:0773440/IV(b)/1> (wherein X represents chlorine or bromine and R a dialkylamino radical or the radical of a saturated heterocyclic secondary base), and the preparation thereof by reacting a 5-halogeno-2-methylindole with formaldehyde and a secondary amine RH in acetic acid solution in approximately equimolar proportions and in the cold (preferably at 0 DEG C.), separating the product by precipitation with dilute caustic soda and crystallizing it from acetone or methyl alcohol. The products are useful pharmaceutically as antagonists to serotonin. Examples describe the preparation 5-chloro- and 5-bromo2 - methyl - 3 - (N - dimethylaminomethyl)-indole and 5 - chloro - 2 - methyl - 3 - piperidinomethylindole. Starting material. 5-Bromo-2-methylindole is prepared by condensing acetone with p-bromophenylhydrazine in aqueous sodium acetate solution and heating the product with anhydrous zinc chloride.
GB19115/55A 1954-07-03 1955-07-01 5-chloro- or bromo-2-methyl-3-(n-substituted-amino-methyl)-indoles and process for their preparation Expired GB773440A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT773440X 1954-07-03

Publications (1)

Publication Number Publication Date
GB773440A true GB773440A (en) 1957-04-24

Family

ID=11316202

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19115/55A Expired GB773440A (en) 1954-07-03 1955-07-01 5-chloro- or bromo-2-methyl-3-(n-substituted-amino-methyl)-indoles and process for their preparation

Country Status (1)

Country Link
GB (1) GB773440A (en)

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