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 preparationInfo
- 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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.
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) |
-
1955
- 1955-07-01 GB GB19115/55A patent/GB773440A/en not_active Expired
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