DE346888C - Process for the preparation of hydrogenated N-alkylpyridine-3-carboxylic acid esters - Google Patents

Process for the preparation of hydrogenated N-alkylpyridine-3-carboxylic acid esters

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Publication number
DE346888C
DE346888C DE1919346888D DE346888DD DE346888C DE 346888 C DE346888 C DE 346888C DE 1919346888 D DE1919346888 D DE 1919346888D DE 346888D D DE346888D D DE 346888DD DE 346888 C DE346888 C DE 346888C
Authority
DE
Germany
Prior art keywords
carboxylic acid
hydrogenated
alkylpyridine
preparation
acid esters
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
DE1919346888D
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German (de)
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.)
RICHARD WOLFFENSTEIN DR
Original Assignee
RICHARD WOLFFENSTEIN DR
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 RICHARD WOLFFENSTEIN DR filed Critical RICHARD WOLFFENSTEIN DR
Application granted granted Critical
Publication of DE346888C publication Critical patent/DE346888C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Verfahren zur Darstellung von hydrierten N-Alkylpyridin-3-carbonsäureestern. Durch Patent 340873 ist ein Verfahren zur Darstellung von hydrierten N-Alkylpyridin-3-carbönsäureestern geschützt. Das Verfahren besteht darin, daß man die N-Halogenalkylate der Pyridin-3-carbonsäurealkylester mit Metallen und einer Halogenwasserstoffsäure in Gegenwart eines nicht hydrolytisch spaltenden Lösungsmittels behandelt.Process for the preparation of hydrogenated N-alkylpyridine-3-carboxylic acid esters. Patent 340873 protects a process for the preparation of hydrogenated N-alkylpyridine-3-carboxylic acid esters. The process consists in treating the N-haloalkylates of the pyridine-3-carboxylic acid alkyl esters with metals and a hydrohalic acid in the presence of a non-hydrolytically cleaving solvent.

Es wurde nun weiter gefunden, daß sich nicht nur die N-Halogenalkylate der Pyridin-3-carbonsäurealkylester, sondern ganz allgemein alle quaternären Ammoniumsalze der N-Alhylpyridin-3-carbonsäurealkylester zur Darstellung _ der hydrierten N-Alkylpyridin-3-carbonsäureester verwenden lassen.It has now been found that not only the N-haloalkylates the pyridine-3-carboxylic acid alkyl ester, but very generally all quaternary ammonium salts the N-Alhylpyridine-3-carboxylic acid alkyl ester for the preparation of the hydrogenated N-alkylpyridine-3-carboxylic acid ester let use.

Beispiel. t.lo g des öligen N-Methylpyrinclin-3-car-13onsättremethylesterinethylsulfates und --9709 granuliertes Zinn , werden mit z 1 Methylalkohol übergossen und unter kräftigem Erwärmen ein starker Strom Salzsäure bis zur Lösung des Zinns und Sättigung mit dem Gas eingeleitet. Nach diesem Zeitraum ist die Reduktion beendet. Das Zinn wird nach einer der gebräuchlichen Methoden entfernt und die entstandene N=Methylhexahydropyridin-3-carbonsäuremethylesterbase abgeschieden. Sie zeigt alle Eigenschaften der aus den N-Halogenalkylaten des Pyridin-3-carbonsäuremethylesters durch Reduktion erhaltenen Verbindung.Example. 100 g of the oily N-methylpyrincline-3-car-13onsättremethylesterinethylsulfate and -9709 granulated tin are poured with z 1 methyl alcohol and a strong current of hydrochloric acid is introduced under vigorous warming until the tin dissolves and saturation with the gas. After this period, the reduction is over. The tin is removed by one of the customary methods and the resulting N = methylhexahydropyridine-3-carboxylic acid methyl ester base is deposited. It shows all the properties of the compound obtained from the N-haloalkylates of pyridine-3-carboxylic acid methyl ester by reduction.

Der N -Äthylhexahydropyridin-3-carbonsäureäthylester wird in ganz genau gleicher Weise wie das im Beispiel beschriebene entsprechende N-1Vlethylderivat erhalten. Er stellt ebenfalls eine basische, ölige Flüssigkeit dar. Die Reduktion mit Magnesium und Salzsäure führt das N-Methylpyridin-3-carbonsäuremethylesterinethylsulfat in eine hydrierte N - Methylpyridin-3-carbonsäuremethylesterbase über. Zu dieser Reduktion verwendet man auf 7 g_ des N-,\lethylsulfats 16 g Magnesium und etwa 150 ccm Methylalkohol.The N -ethylhexahydropyridine-3-carboxylic acid ethyl ester is in whole exactly the same way as the corresponding N-1Vlethylderivat described in the example obtain. It is also a basic, oily liquid. The reduction with magnesium and hydrochloric acid, methyl N-methylpyridine-3-carboxylate leads to ethyl sulfate into a hydrogenated N-methylpyridine-3-carboxylic acid methyl ester base. To this Reduction is used to 7 g of the N -, \ lethylsulfat 16 g of magnesium and about 150 cc of methyl alcohol.

Die so erhaltenen Produkte sollen als Ausgangsstoffe für die Darstellung therapeutisch wertvoller Produkte dienen.The products obtained in this way are intended as starting materials for the representation serve therapeutically valuable products.

Claims (1)

PATENTANSPRUCH: Abänderung des durch Patent 3.1o873 geschützten Verfahrens zur Darstellung von hydrierten N-Alkylpyridin-3-carbonsäureestern, darin bestehend, daß man an Stelle der N-Halogenalkylate der Pyridin-3-carbonsäurealkylester andere quaternäre Ammoniumsalze dieser Aminosäureester verwendet. PATENT CLAIM: Modification of the process protected by patent 3.1o873 for the preparation of hydrogenated N-alkylpyridine-3-carboxylic acid esters, consisting in using other quaternary ammonium salts of these amino acid esters instead of the N-haloalkylates of the pyridine-3-carboxylic acid alkyl esters.
DE1919346888D 1919-10-23 1919-10-23 Process for the preparation of hydrogenated N-alkylpyridine-3-carboxylic acid esters Expired DE346888C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE346888T 1919-10-23

Publications (1)

Publication Number Publication Date
DE346888C true DE346888C (en) 1922-01-07

Family

ID=6255621

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1919346888D Expired DE346888C (en) 1919-10-23 1919-10-23 Process for the preparation of hydrogenated N-alkylpyridine-3-carboxylic acid esters

Country Status (1)

Country Link
DE (1) DE346888C (en)

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