CH313682A - Verfahren zur Herstellung eines neuen Tetrahydropyridins - Google Patents

Verfahren zur Herstellung eines neuen Tetrahydropyridins

Info

Publication number
CH313682A
CH313682A CH313682DA CH313682A CH 313682 A CH313682 A CH 313682A CH 313682D A CH313682D A CH 313682DA CH 313682 A CH313682 A CH 313682A
Authority
CH
Switzerland
Prior art keywords
tetrahydropyridins
zur herstellung
verfahren zur
herstellung eines
radicals
Prior art date
Application number
Other languages
German (de)
French (fr)
Inventor
Karl Dr Hoffmann
Eugen Dr Tagmann
Ernst Dr Urech
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH313682A publication Critical patent/CH313682A/en

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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • 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
    • C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—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 two 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 directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Description

  

      Verfahren    zur Herstellung     eines    neuen     Tetrahydropyridins       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung von     3-Phenyl-          3-methyl-2,6-dioxo-I.,2,3,6        -tetrahydro    -     pyridin,     welches dadurch     gekennzeichnet    ist, dass man  in einer Verbindung der Formel  
EMI0001.0009     
    worin X und Y unter     Ausbildung    einer     Dop-          pelbindung        abspaltbare        Reste    bedeuten,

   X  und Y unter     Ausbildung    einer Doppelbindung  abspaltet. Dabei bedeutet vorzugsweise einer  der Reste X und Y     Wasserstoff    und der  andere eine     reaktionsfähige    veresterte     Oxy-          gruppe,    wie eine mit starken anorganischen  oder organischen Säuren, z. B.     Halogenwasser-          stoffsäuren    oder anorganische oder organische       Sulfonsäuren,    veresterte     Oxygruppe.    Die Ab  spaltung von X und     Y    geschieht in diesem  Fall vorteilhaft in Anwesenheit.     säurebinden-          der    Mittel.

    



  Als solche Mittel kommen zum Beispiel  Basen, wie     Pyridin,        Collidin    oder konzen  trierte     wässerige    Alkalien, in Betracht.    <I>Beispiel.</I>  2,8 Gewichtsteile     2,6-Dioxo-3-methyl-3-          phenyl-brompiperidin        werden    mit 10,0     Volum-          teilen        Collidin    während 150 Minuten unter       Rückfluss    in einem Ölbad von 150  erhitzt.

    Sodann wird das     Collidin    im     Vakuum    ab  destilliert und der Rückstand in Äther auf  genommen, mit     'Nasser,        verd.        Salzsäure    und       wiederum        mit        Wasser        gewaschen,          und        der    Äther abgedampft, worauf der     Rüek-          sta.nd    aus Äther umkristallisiert wird.

   Das so  erhaltene     3-Metliyl-3-phenyl-2,6-dioxo-1,2,3,6-          tetrahydro-pyridin    der Formel  
EMI0001.0052     
    schmilzt bei     160-164 .     



  Das als     Ausgangsprodukt    verwendete     2,6-          Dioxo-3-methyl-3-phenyl-brompiperidin    vom       F.=148-1540    kann man durch     Bromiereii     von     2,6-Dioxo-3-methyl-3-phenyl-piperidin    mit  Brom unter     Beliehtung    herstellen.



      Process for the preparation of a new tetrahydropyridine The subject of the present patent is a process for the preparation of 3-phenyl-3-methyl-2,6-dioxo-I., 2,3,6 -tetrahydropyridine, which is characterized in that one in a compound of the formula
EMI0001.0009
    where X and Y are radicals which can be split off with formation of a double bond,

   X and Y are split off with the formation of a double bond. One of the radicals X and Y is preferably hydrogen and the other is a reactive esterified oxy group, such as one with strong inorganic or organic acids, e.g. B. hydrogen halide acids or inorganic or organic sulfonic acids, esterified oxy group. From the cleavage of X and Y takes place in this case advantageously in the presence. acid-binding agents.

    



  Bases such as pyridine, collidine or concentrated aqueous alkalis, for example, come into consideration as such agents. <I> Example. </I> 2.8 parts by weight of 2,6-dioxo-3-methyl-3-phenyl-bromopiperidine are refluxed with 10.0 parts by volume of collidine in a 150-meter oil bath for 150 minutes.

    The collidine is then distilled off in vacuo and the residue is taken up in ether, washed with water, dilute hydrochloric acid and again with water, and the ether is evaporated, whereupon the residue is recrystallized from ether.

   The 3-methyl-3-phenyl-2,6-dioxo-1,2,3,6-tetrahydropyridine of the formula obtained in this way
EMI0001.0052
    melts at 160-164.



  The 2,6-dioxo-3-methyl-3-phenyl-bromopiperidine of F. = 148-1540 used as starting product can be obtained by bromination of 2,6-dioxo-3-methyl-3-phenyl-piperidine with bromine under exposure produce.

Claims (1)

PATENTANSPRUCI3 Verfahren zur Herstellung von 3-Phenyl- 3-niethy 1-2,6-dioxo-1,2,3,6 -tet.rahydro -pyridin, dadurch gekennzeichnet, dass man in einer Verbindung der Formel EMI0002.0003 worin X und Y unter Ausbildung einer Dop pelbindung abspaltbare Reste bedeuten, X und Y unter Ausbildung einer Doppelbindung abspaltet. UNTERANSPRÜCI3E 1. PATENT claims Process for the preparation of 3-phenyl-3-niethy 1-2,6-dioxo-1,2,3,6 -tet.rahydro-pyridine, characterized in that a compound of formula EMI0002.0003 where X and Y denote radicals which can be split off with formation of a double bond, and X and Y denote off with formation of a double bond. SUBClaims 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Verbindungen verwendet, in welchen einer der Reste X und Y 'Wasserstoff und der andere eine reaktions- fähige veresterte Oxygruppe bedeutet. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man Verbindungen verwendet, in welchen einer der Reste X und Y -Wasserstoff und der andere Brom bedeutet. 3. Verfahren nach Patentanspruch und den Unteransprüehen 1 und 2, dadurch ge kennzeichnet, dass man in Anwesenheit eines säurebindenden Mittels arbeitet. Process according to patent claim, characterized in that compounds are used in which one of the radicals X and Y 'is hydrogen and the other is a reactive esterified oxy group. 2. The method according to claim and dependent claim 1, characterized in that compounds are used in which one of the radicals X and Y is hydrogen and the other is bromine. 3. The method according to claim and the dependent claims 1 and 2, characterized in that one works in the presence of an acid-binding agent.
CH313682D 1952-04-03 1952-04-03 Verfahren zur Herstellung eines neuen Tetrahydropyridins CH313682A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH313682T 1952-04-03

Publications (1)

Publication Number Publication Date
CH313682A true CH313682A (en) 1956-04-30

Family

ID=4495294

Family Applications (1)

Application Number Title Priority Date Filing Date
CH313682D CH313682A (en) 1952-04-03 1952-04-03 Verfahren zur Herstellung eines neuen Tetrahydropyridins

Country Status (1)

Country Link
CH (1) CH313682A (en)

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