CH269656A - Process for the preparation of a new piperidine compound. - Google Patents

Process for the preparation of a new piperidine compound.

Info

Publication number
CH269656A
CH269656A CH269656DA CH269656A CH 269656 A CH269656 A CH 269656A CH 269656D A CH269656D A CH 269656DA CH 269656 A CH269656 A CH 269656A
Authority
CH
Switzerland
Prior art keywords
preparation
piperidine compound
new piperidine
phenyl
acetic acid
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 CH269656A publication Critical patent/CH269656A/en

Links

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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/02—Preparation by ring-closure or hydrogenation

Description

  

      Verfahren        zur    Herstellung     einer    neuen     Piperidinverbindung.       Das vorliegende Patent betrifft ein Ver  fahren zur     Herstellung    einer neuen     Piperidin-          verbindung,    welches dadurch gekennzeichnet.  ist, dass man Verbindungen der Formeln  
EMI0001.0008     
    worin X und Y mit Ausnahme eines in einem  von ihnen enthaltenen Sauerstoffatoms sieh  bei der Reaktion abspaltende Reste bedeuten,  miteinander umsetzt,     wie    z.

   B. einerseits a  Phenyl-a-piperidyl-(2)-essigsäure oder ihre  funktionellen Derivate, wie ihre     Halogenide,     ihr     Anhydrid    oder ihre Ester und anderseits  Methanol bzw. seine     reaktionsfähigen    Ab  kömmlinge, wie z. B. seine     Metallalkoholate.     Dabei kann man auch vom     a-Phenyl-a-piperi-          clyl-(2)-essigsäurenitril    ausgehen und dieses  in Gegenwart des Methanols bzw. eines Deri  vates desselben in die Säure bzw. eine andere  Verbindung der obigen Formel überführen.  



  Die Reaktion kann in Gegenwart eines Lö  sungsmittels     und/oder    Katalysators oder Kon  densationsmittels durchgeführt werden.  



  Der so erhaltene     a-Phenyl-a-piperidyl-(2)-          essigsäuremethylester    besitzt den Kp.     o,"    135  bis 137  und bildet ein     Hydrochlorid    vom    F. 208 . Er soll als Heilmittel Verwendung  finden.  



       Beispiel:     100     Gew.-Teile        a-Phenyl-a-piperidyl-(2)-          essigsäure-hydrochlorid    vom     Zersetzungspunkt     248  (erhalten z. B. durch Hydrierung von       aLPhenyl-a-p3ridyl-(2)-acetamid    mit Platin  katalysator und anschliessende     Verseifung    mit  kochender     HCl)    werden in 200     Vol.-Teilen     Methanol gelöst und während 2 bis 3 Stunden  am     Rückfluss    mit     Chlorwasserstoffgas    behan  delt.

   Nach     Einengen,    Verdünnen mit Was  ser und     Alkalisehmaehen    mit Soda wird das  zurückbleibende öl in Äther aufgenommen,  getrocknet und im     Hoehvakuum    destilliert.  Der a -     Phen        t-1-    a -     piper        idyl    - (2) -     essigsäure-          methylester    geht unter 0,6 mm Quecksilber  druck bei 135 bis 137  über. Er bildet ein       Hydrochlorid    vom F.     Z08 .  



      Process for the preparation of a new piperidine compound. The present patent relates to a process for the preparation of a new piperidine compound, which is characterized. is that you can get compounds of the formulas
EMI0001.0008
    wherein X and Y, with the exception of an oxygen atom contained in one of them, mean radicals which split off during the reaction, reacts with one another, such as.

   B. on the one hand a phenyl-a-piperidyl- (2) -acetic acid or its functional derivatives, such as their halides, their anhydride or their esters and on the other hand methanol or its reactive From comers such. B. its metal alcoholates. It is also possible to start from the α-phenyl-α-piperi- clyl- (2) -acetic acid nitrile and convert this into the acid or another compound of the above formula in the presence of methanol or a derivative thereof.



  The reaction can be carried out in the presence of a solvent and / or catalyst or condensation agent.



  The a-phenyl-a-piperidyl- (2) - acetic acid methyl ester obtained in this way has the bp. O, "135 to 137 and forms a hydrochloride of F. 208. It is said to be used as a medicinal product.



       Example: 100 parts by weight of a-phenyl-a-piperidyl- (2) -acetic acid hydrochloride with a decomposition point of 248 (obtained, for example, by hydrogenation of aL-phenyl-a-p3ridyl- (2) -acetamide with platinum catalyst and subsequent Saponification with boiling HCl) are dissolved in 200 parts by volume of methanol and treated under reflux with hydrogen chloride gas for 2 to 3 hours.

   After concentration, dilution with water and alkali milling with soda, the remaining oil is taken up in ether, dried and distilled in a high vacuum. The a - phen t-1 - a - piperidyl - (2) - acetic acid methyl ester goes over at 135 to 137 under 0.6 mm mercury pressure. It forms a hydrochloride from F. Z08.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer neuen Piperidinverbindung, dadurch gekennzeichnet, dass man Verbindungen der Formeln EMI0001.0045 worin X und Y mit Ausnahme eines in einem von ihnen enthaltenen Sauerstoffatoms sieh bei der Reaktion abspaltende Reste bedeuten, miteinander umsetzt. Der so erhaltene a-Phenyl-a-piperidyl-(2)- essigsäuremethylester besitzt den Kp. o,, <B>135</B> bis 137 und bildet ein Hydrochlorid vom F. 208 . Er soll als Heilmittel Verwendung finden. PATENT CLAIM: Process for the preparation of a new piperidine compound, characterized in that compounds of the formulas EMI0001.0045 where X and Y, with the exception of an oxygen atom contained in one of them, are radicals which split off during the reaction, are reacted with one another. The methyl a-phenyl-a-piperidyl- (2) - acetic acid methyl ester obtained in this way has the bp. O ,, 135 to 137 and forms a hydrochloride of 208. It is said to be used as a remedy.
CH269656D 1944-01-19 1944-01-19 Process for the preparation of a new piperidine compound. CH269656A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH269656T 1944-01-19

Publications (1)

Publication Number Publication Date
CH269656A true CH269656A (en) 1950-07-15

Family

ID=4477366

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269656D CH269656A (en) 1944-01-19 1944-01-19 Process for the preparation of a new piperidine compound.

Country Status (1)

Country Link
CH (1) CH269656A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0881216A1 (en) * 1997-05-30 1998-12-02 Johnson Matthey Public Limited Company Solid methylphenidate, its preparation and use in medicine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0881216A1 (en) * 1997-05-30 1998-12-02 Johnson Matthey Public Limited Company Solid methylphenidate, its preparation and use in medicine
US6096760A (en) * 1997-05-30 2000-08-01 Johnson Matthey Public Limited Company Solid α-phenyl-2-piperidine acetate free base, its preparation and use in medicine

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