GB696862A - Manufacture of new methylpyridines - Google Patents
Manufacture of new methylpyridinesInfo
- Publication number
- GB696862A GB696862A GB20041/51A GB2004151A GB696862A GB 696862 A GB696862 A GB 696862A GB 20041/51 A GB20041/51 A GB 20041/51A GB 2004151 A GB2004151 A GB 2004151A GB 696862 A GB696862 A GB 696862A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylpyridine
- piperidino
- ethyl
- ethylamino
- prepared
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention comprises 6-[N-(b -piperidinoethyl)-N-alkylamino]-methylpyridines of the general formula <FORM:0696862/IV (b)/1> wherein the alkyl group contains 1 to 3 carbon atoms and the methyl group occupies the 2- or 4-position of the pyridine nucleus, and acid addition salts thereof, and a process for the preparation of the above compounds by reacting the required 6-alkylamino methylpyridine, or an N-alkali metal derivative thereof, with a b -piperidino-ethyl halide, e.g. the chloride or bromide, or by reacting the required 6-(b -piperidino-ethylamino)-methylpyridine with an alkyl halide, e.g. the chloride, bromide or iodide. The above reactions are preferably carried out in a hydrocarbon solvent, e.g. benzene or toluene, and in the presence of an alkali metal amide or hydride, e.g. sodamide or lithium amide or sodium or lithium hydride. The reaction temperatures may be in the range 75 DEG to 150 DEG C. and preferably from 100 DEG to 120 DEG C. Acid addition salts are formed by normal methods. In the examples the following compounds are prepared: 6-[N-(b -piperidino-ethyl)-N-methyl-amino]-2-methylpyridine and its salts derived from hydrochloric, sulphuric, tartaric, maleic and citric acid, 6-[N-(b -piperidino - ethyl) - N - isopropylamino] - 4 - methylpyridine and its hydrochloride salt, 6 - [N - (b - piperidino - ethyl) - N - ethylamino] - 4 - methylpyridine and its hydrochloride salt, and 6 - (N - (b - piperidino - ethyl) - N - n - propylamino] - 4 - methylpyridine and its hydrochloride salt. The following compounds are also mentioned: 6-[N-(b -piperidino-ethyl)-N methylamino] - 4 - methylpyridine, 6 - [N - (b - piperidino - ethyl) - N - isopropylamino] - , 6 - [N - (b - piperidino - ethyl) - N - ethylamino] -, and 6 - [N - (b - piperidino - ethyl) - N - n - propylamino] - 2 - methylpyridine. Similar 2-and 4-methylpyridine derivatives may be prepared having an N-methyl, ethyl and isopropyl radical. 6 - Ethylamino - and 6 - isopropylamino - 4 - methylpyridine are prepared from the reaction of 6-amino-4-methylpyridine and sodamide and adding ethyl iodide and isopropyl bromide respectively to the reaction mixture. 6 - Methylamino - 2 - methylpyridine is prepared by a similar method using methyl iodide. 6 - (b - Piperidino - ethylamino) - 4 - methylpyridine is prepared from the reaction of sodamide and 6-amino-4-methylpyridine and adding b -piperidino-ethyl chloride to the reaction mixture.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US696862XA | 1950-08-25 | 1950-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB696862A true GB696862A (en) | 1953-09-09 |
Family
ID=22090584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20041/51A Expired GB696862A (en) | 1950-08-25 | 1951-08-24 | Manufacture of new methylpyridines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB696862A (en) |
-
1951
- 1951-08-24 GB GB20041/51A patent/GB696862A/en not_active Expired
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