CH304557A - Process for the preparation of a new tetrahydropyridine. - Google Patents

Process for the preparation of a new tetrahydropyridine.

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Publication number
CH304557A
CH304557A CH304557DA CH304557A CH 304557 A CH304557 A CH 304557A CH 304557D A CH304557D A CH 304557DA CH 304557 A CH304557 A CH 304557A
Authority
CH
Switzerland
Prior art keywords
tetrahydropyridine
radicals
preparation
compound
process according
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
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 CH304557A publication Critical patent/CH304557A/en

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  • Hydrogenated Pyridines (AREA)

Description

  

  Verfahren zur Herstellung     eines    neuen     Tetrahydropyridins.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung des im Schweiz.  Patent Nr. 301584 beschriebenen     Tetrahydro-          pyridins,    welches dadurch gekennzeichnet ist,  dass man in einer Verbindung der Formel  
EMI0001.0005     
    worin X und Y bei der Reaktion unter Ausbil  dung einer Doppelbindung     abspaltbare    Reste  bedeuten, X und Y unter Ausbildung einer Dop  pelbindung abspaltet.

   Dabei bedeutet vorzugs  weise einer der Reste X und Y     'yffasserstoff     und der andere eine reaktionsfähige veresterte       nxygruppe,    wie eine mit starken anorgani  schen oder organischen Säuren, z. B. Halogen  wasserstoffsäuren oder     anorganischen    oder  organischen     Sulfonsäi@ren,    veresterte     Oxy-          gruppe.    Die Abspaltung von X und Y ge  schieht. vorteilhaft in     Anwesenheit    säurebin  dender Mittel.  



  Als solche Mittel kommen z. B. Basen,     wie          Pyridin,        Collidin    oder konzentrierte     wässrige     Alkalien, in Betracht.  



       Beispiel:     3,0 Gewichtsteile     2,6-Dioxo-3-äthyl-3-phe-          nyl-brom-piperidin    werden mit 10,0     Volum-          t.eilen        Collidin    während 30 bis 60 Minuten  unter     Rüeldluss    in einem Ölbad von 150  er-         hitzt.    Sodann wird das     Collidin    im Vakuum       abdestilliert    und der Rückstand in Essigester  und Wasser gelöst. Die     Essigesterlösung    wird  getrocknet, filtriert und auf ein kleines Vo  lumen eingeengt, dann zur Kristallisation ge  bracht.

   Das so erhaltene     3-Äthyl-3-phenyl-2,6-          dioxo-1,2,3,6-tetrahydro-pyridin    der Formel  
EMI0001.0031     
    schmilzt bei 164 bis 166 .  



  Das als Ausgangsprodukt verwendete     2,6-          Dioxo-3-äthyl-3-phenyl-brompiperidin    vom  F. = 164 bis 166  kann man durch     Bromie-          ren    von     2,6-Dioxo-3-äthyl-3-phenyl-piperidin     mit Brom unter Belichtung herstellen.



  Process for the preparation of a new tetrahydropyridine. The subject of the present patent is a process for the production of the in Switzerland. Patent No. 301584 described tetrahydropyridine, which is characterized in that in a compound of the formula
EMI0001.0005
    wherein X and Y are radicals which can be split off in the reaction to form a double bond, and X and Y to split off with formation of a double bond.

   It preferably means one of the radicals X and Y 'hydrogen and the other a reactive esterified nxygruppe, such as one with strong inorganic or organic acids, z. B. Hydrogen halides or inorganic or organic sulfonic acids, esterified oxy groups. The splitting off of X and Y happens. advantageously in the presence of acid-binding agents.



  As such means come z. B. bases, such as pyridine, collidine or concentrated aqueous alkalis, into consideration.



       Example: 3.0 parts by weight of 2,6-dioxo-3-ethyl-3-phenyl-bromopiperidine are mixed with 10.0 parts by volume of collidine for 30 to 60 minutes under pressure in an oil bath of 150 heats. The collidine is then distilled off in vacuo and the residue is dissolved in ethyl acetate and water. The ethyl acetate solution is dried, filtered and concentrated to a small volume, then brought to crystallization.

   The 3-ethyl-3-phenyl-2,6-dioxo-1,2,3,6-tetrahydropyridine of the formula obtained in this way
EMI0001.0031
    melts at 164 to 166.



  The 2,6-dioxo-3-ethyl-3-phenyl-bromopiperidine with a melting point of 164 to 166 used as the starting product can be obtained by brominating 2,6-dioxo-3-ethyl-3-phenyl-piperidine with bromine produce under exposure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des im Schweiz. Patent Nr. 301584 beschriebenen Tetrahydro- pyridins, dadurch gekennzeichnet, dass man in einer Verbindung der Formel EMI0001.0042 worin X und Y bei der Reaktion unter Aus- bildurig einer Doppelbindung abspaltbare Reste bedeuten, X und Y unter Ausbildung einer Doppelbindung abspaltet. UN TERANSPRi'C11E 1. PATENT CLAIM: Process for the production of the in Switzerland. Patent No. 301584 described tetrahydropyridine, characterized in that in a compound of the formula EMI0001.0042 in which X and Y are radicals which can be split off in the reaction with the formation of a double bond, and X and Y are split off with the formation of a double bond. UN TERANSPRi'C11E 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man eine Verbin dung verwendet, in welcher einer der Reste X und Y Wasserstoff und der andere eine reak tionsfähige veresterte Oxygruppe bedeutet. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass ma=n eine Verbindung verwendet, in welcher einer der Reste X und Y Wasserstoff und der andere Brom bedeutet.. 3. Process according to claim, characterized in that a compound is used in which one of the radicals X and Y is hydrogen and the other is a reactive esterified oxy group. Process according to claim and dependent claim 1, characterized in that ma = n uses a compound in which one of the radicals X and Y is hydrogen and the other is bromine. 3. Verfahren nach Patentansprueli und den Unteransprüchen 1 und 2, dadurch ge kennzeichnet, dass man in Anwesenheit eines säurebindenden Mittels arbeitet. Process according to patent claims and the dependent claims 1 and 2, characterized in that one works in the presence of an acid-binding agent.
CH304557D 1951-04-28 1951-04-28 Process for the preparation of a new tetrahydropyridine. CH304557A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH304557T 1951-04-28

Publications (1)

Publication Number Publication Date
CH304557A true CH304557A (en) 1955-01-15

Family

ID=4492117

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304557D CH304557A (en) 1951-04-28 1951-04-28 Process for the preparation of a new tetrahydropyridine.

Country Status (1)

Country Link
CH (1) CH304557A (en)

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