CH150168A - Process for the preparation of a basic ether of the pyridine series. - Google Patents

Process for the preparation of a basic ether of the pyridine series.

Info

Publication number
CH150168A
CH150168A CH150168DA CH150168A CH 150168 A CH150168 A CH 150168A CH 150168D A CH150168D A CH 150168DA CH 150168 A CH150168 A CH 150168A
Authority
CH
Switzerland
Prior art keywords
preparation
pyridine series
basic ether
ether
pyridone
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH150168A publication Critical patent/CH150168A/en

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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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     basischen    Äthers der     Pyridinreihe.       Es wurde gefunden, dass man zu einem  basischen Äther der     Pyridinreihe    gelangen  kann, wenn man .einen Ester des     Diäthyl-          aminoäthanols    auf     2-Pyridon    in Gegenwart  säurebindender Mittel     einwirken    lässt.  



  Das entstandene     2-Diäthylaminoäthoxy-          pyridin    bildet ein     farbloses    Öl vom     Sdp.    98  bis<B>100'</B> bei 2 mm Druck. Es ist in Wasser  leicht löslich. Das farblose     Monochlorhydrat     der Base .schmilzt bei 135  .  



  Die neue Base soll als solche oder als  Zwischenprodukt für therapeutische Zwecke       Verwendung    finden.  



       Beispiel:     Man gibt 38 Teile     2-Pyridon    zu einer al  koholischen Lösung von 9,2 Teilen Natrium.  Hierauf destilliert man den Alkohol ab und  erhitzt nach Zusatz von     Toluol    mit 70; Teilen       Chloräthyldiäthylamin.    Nach beendeter  Reaktion wird das     Lösungsmittel    abgetrie  ben und der Rückstand vom gleichzeitig    sich bildenden, höher siedenden     N-Diäthy        1-          aminoäthyl-2-pyridon    getrennt. Dies ge  schieht entweder durch     Wasserdampfdestil-          lation,    wobei der Äther überdestilliert, oder  durch Fraktionierung.

   Die bei 95-105  unter 2 mm Druck siedende Fraktion wird  gesondert aufgefangen und durch nochmalige  Destillation in reiner Form erhalten.  



  Als säurebindende Mittel können zum  Beispiel auch     Alkalihydroxyde    oder     -kar-          bonate    Verwendung finden. Ebenso lässt  sich das     Toluol    durch andere Lösungsmittel,  zum Beispiel durch Alkohol, Aceton oder  Wasser, ersetzen.  



  An Stelle des     Chlorides    können auch an  dere Ester des     Diäthylaminoäthanols,    zum  Beispiel das     Bromid    oder aromatische     Sulfo-          säureester,    Verwendung finden.



  Process for the preparation of a basic ether of the pyridine series. It has been found that a basic ether of the pyridine series can be obtained if an ester of diethyl aminoethanol is allowed to act on 2-pyridone in the presence of acid-binding agents.



  The 2-diethylaminoethoxypyridine formed forms a colorless oil with a boiling point of 98 to 100 under a pressure of 2 mm. It is easily soluble in water. The colorless monochlorohydrate of the base melts at 135.



  The new base is intended to be used as such or as an intermediate for therapeutic purposes.



       Example: 38 parts of 2-pyridone are added to an alcoholic solution of 9.2 parts of sodium. The alcohol is then distilled off and, after addition of toluene, heated at 70; Parts of chloroethyl diethylamine. After the reaction has ended, the solvent is removed and the residue is separated from the higher-boiling N-diethy 1- aminoethyl-2-pyridone which is formed at the same time. This is done either by steam distillation, with the ether distilling over, or by fractionation.

   The fraction which boils at 95-105 under 2 mm pressure is collected separately and obtained in pure form by repeated distillation.



  Alkali hydroxides or carbonates, for example, can also be used as acid-binding agents. The toluene can also be replaced by other solvents, for example alcohol, acetone or water.



  Other esters of diethylaminoethanol, for example bromide or aromatic sulfonic acid esters, can also be used in place of the chloride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basi schen Äthers der Pyridinreihe, dadurch ge kennzeichnet, dass man Ester des Diäthyl- aminoäthanols auf 2-Pyridon in Gegenwart säurebindender Mittel einwirken lässt. Das entstandene 2-Diäthylaminoäthoxy- pyridin bildet ein farbloses 01 vom Sdp. 98 bis<B>10,0'</B> bei 2 mm Druck. Es ist in Wasser leicht löslich. Das farblose Monochlorhydrat der Base schmilzt bei 185 . PATENT CLAIM: Process for the preparation of a basic ether of the pyridine series, characterized in that esters of diethyl aminoethanol are allowed to act on 2-pyridone in the presence of acid-binding agents. The 2-diethylaminoethoxypyridine formed forms a colorless oil with a boiling point of 98 to 10.0 'at 2 mm pressure. It is easily soluble in water. The colorless monochlorohydrate of the base melts at 185. Die neue Base soll als solche oder als Zwischenprodukt für therapeutische Zwecke Verwendung finden. The new base is intended to be used as such or as an intermediate for therapeutic purposes.
CH150168D 1929-08-10 1929-08-10 Process for the preparation of a basic ether of the pyridine series. CH150168A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH146546T 1929-08-10
CH150168T 1929-08-10

Publications (1)

Publication Number Publication Date
CH150168A true CH150168A (en) 1931-10-15

Family

ID=25714875

Family Applications (1)

Application Number Title Priority Date Filing Date
CH150168D CH150168A (en) 1929-08-10 1929-08-10 Process for the preparation of a basic ether of the pyridine series.

Country Status (1)

Country Link
CH (1) CH150168A (en)

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