CH193773A - Process for the preparation of 2,4-dioxo-3,3-diethyl-5-chloro-tetrahydropyridine. - Google Patents

Process for the preparation of 2,4-dioxo-3,3-diethyl-5-chloro-tetrahydropyridine.

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Publication number
CH193773A
CH193773A CH193773DA CH193773A CH 193773 A CH193773 A CH 193773A CH 193773D A CH193773D A CH 193773DA CH 193773 A CH193773 A CH 193773A
Authority
CH
Switzerland
Prior art keywords
diethyl
dioxo
tetrahydropyridine
chloro
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH193773A publication Critical patent/CH193773A/en

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Description

  

  Verfahren zur Darstellung von     2,4-Dioxo-3,3-diäthyl-ü-ehlor-tetrahydropyridin.       Es wurde gefunden, dass .durch die Ein  wirkung     halogenierend    wirkender Mittel auf       2,4-Diogo-3,3-dialkyl-tetrahydropyridine    in  glatt verlaufender     Umsetzung    der Wasser  stoff in der     5-Stellung    durch Halogen sub  stituiert werden kann. Mit den 1- .oder     6-          Methyl-        bezw.        1;6-Dimethylverbindungen     verläuft die Umsetzung durchaus gleichsinnig  und     führt    zu gleichartigen Verbindungen.

    Die Ausgangsstoffe gewinnt man nach den  Verfahren des schweizerischen Patentes  Nr. 18782,6 und seiner Zusätze, sowie der  deutschen Patente Nr.     637385    und Nr.     638532..     Es ist     überraechen.d,    dass bei diesen Umset  zungen     Substitution    erfolgt und     nicht    Addi  tion. Man kann darin auch kein -dem     Py-          ridin    ähnliches Verhalten erblicken, denn die       Halogenierungen    verlaufen rasch und glatt  unter sehr milden     Bedingungen.    Diese wer  den deshalb vorzugsweise bei niedrigen Tem  peraturen     unter    Anwendung von Lösungs  mitteln vorgenommen.

      Gegenstand des vorliegenden     Patentes    ist       ein    Verfahren zur Darstellung von     2,4-Di-          ogo-3,3-diäthyl-5-chlortetrahydropyridin,    wel  ches dadurch     gekennzeichnet    ist, dass auf     2,4-          Diogo-3,3-diäthyltetrahydropyridin    Chlor  einwirken     gelassen    wird.  



  Das neue     2,4-Dio$o-3,3-.diäthyl-5-chlor-          tetrahydropyridin    bildet farblose Kristalle,  die bei 116 bis 117   schmelzen und in den  gebräuchlichen organischen     Lösungsmitteln     leicht löslich sind. In wässerigen Alkalien  löst sich die Verbindung unverändert mit  gelblicher Farbe. Sie wirkt schlafmachend  und soll als Arzneimittel verwendet werden.    <I>Beispiel:</I>    Man löst 167     Gewichtsteile        2,4-Diogo-3,3-          diäthyltetrahydropyridin    in 700     Volumteilen     80%iger Essigsäure. Unter Eiskühlung von  aussen und gutem Rühren leitet man in diese  Lösung 71     Gewichtsteile    Chlor ein.

   Das  Chlor wird sofort aufgenommen. Nach be-           endetem    Einleiten wird die     Lösung        unter        ver-          mindertem    Druck bis fast zur Trockne ein  gedampft, der     Rückstand    mit Wasser ange  rieben und das sofort     kristallin    erstarrende       2,4-Dioxo-3,3-diäthyl-.5-chlor-tetrahydropyri-          din    von der wässerigen Flüssigkeit getrennt.  Zur völligen Reinigung kann man aus ver  dünntem Methanol     umlösen.  



  Process for the preparation of 2,4-dioxo-3,3-diethyl-ü-ehlor-tetrahydropyridine. It has been found that the action of halogenating agents on 2,4-diogo-3,3-dialkyl-tetrahydropyridines can be substituted for the hydrogen in the 5-position by halogen in a smooth reaction. With the 1-. Or 6-methyl or. 1; 6-dimethyl compounds, the reaction proceeds in the same direction and leads to similar compounds.

    The starting materials are obtained according to the process of Swiss patent No. 18782.6 and its additives, as well as German patents No. 637385 and No. 638532 .. It is surprising that in these implementations there is substitution and not addition. Nor can one see any behavior similar to that of pyridine, for the halogenations proceed quickly and smoothly under very mild conditions. These who are therefore preferably made at low temperatures using solvents.

      The subject of the present patent is a method for the preparation of 2,4-diogo-3,3-diethyl-5-chlorotetrahydropyridine, wel ches is characterized in that chlorine is allowed to act on 2,4-diogo-3,3-diethyltetrahydropyridine becomes.



  The new 2,4-Dio $ o-3,3-.diethyl-5-chloro-tetrahydropyridine forms colorless crystals which melt at 116 to 117 and are easily soluble in the common organic solvents. In aqueous alkalis, the compound dissolves unchanged with a yellowish color. It has a sleep-inducing effect and is intended to be used as a medicine. <I> Example: </I> 167 parts by weight of 2,4-diogo-3,3-diethyltetrahydropyridine are dissolved in 700 parts by volume of 80% acetic acid. With ice-cooling from the outside and thorough stirring, 71 parts by weight of chlorine are passed into this solution.

   The chlorine is absorbed immediately. When the introduction is complete, the solution is evaporated to almost dryness under reduced pressure, the residue is rubbed with water and the 2,4-dioxo-3,3-diethyl-.5-chloro-tetrahydropyri- din separated from the aqueous liquid. For complete cleaning you can dissolve from ver diluted methanol.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 2,4-Diogo- 3;3 - diäthyl - 5 - chlor-tetrahydropyridin,da- durch gekennzeichnet, -dass auf 2,4-Dioxo-3,3- .diäthyltetrahydropyridin Chlor einwirken ge lassen wird. PATENT CLAIM: Process for the preparation of 2,4-diogo- 3; 3-diethyl-5-chloro-tetrahydropyridine, characterized in that chlorine is allowed to act on 2,4-dioxo-3,3-. Diethyltetrahydropyridine. Das neue 2,4- Dioxo-3,3-diäthyl-5-chlor- tetrahy dropyridin bildet farblose Kristalle, ,die bei 116 bis 11? schmelzen und in .den gebräuchlichen organischen Lösungsmitteln leicht löslich sind. In wässerigen Alkalien löst sich die Verbindung unverändert mit gelblicher Farbe. Sie wirkt schlafmachend und soll als Arzneimittel verwendet werden. The new 2,4-dioxo-3,3-diethyl-5-chlorotetrahy dropyridine forms colorless crystals, which at 116 to 11? melt and are easily soluble in common organic solvents. In aqueous alkalis, the compound dissolves unchanged with a yellowish color. It has a sleep-inducing effect and is intended to be used as a medicine.
CH193773D 1936-04-25 1937-02-26 Process for the preparation of 2,4-dioxo-3,3-diethyl-5-chloro-tetrahydropyridine. CH193773A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE193773X 1936-04-25

Publications (1)

Publication Number Publication Date
CH193773A true CH193773A (en) 1937-10-31

Family

ID=5740813

Family Applications (1)

Application Number Title Priority Date Filing Date
CH193773D CH193773A (en) 1936-04-25 1937-02-26 Process for the preparation of 2,4-dioxo-3,3-diethyl-5-chloro-tetrahydropyridine.

Country Status (1)

Country Link
CH (1) CH193773A (en)

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