CH247927A - Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. - Google Patents

Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.

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Publication number
CH247927A
CH247927A CH247927DA CH247927A CH 247927 A CH247927 A CH 247927A CH 247927D A CH247927D A CH 247927DA CH 247927 A CH247927 A CH 247927A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
ester
cycloalkyl
aryl
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R 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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH247927A publication Critical patent/CH247927A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Description

  

      Verfahren    zur Darstellung eines basischen Esters einer 1     Aryl-cycloalkyl-1-carbonsäure.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Darstellung eines     basischen     Esters einer     1-Aryl-eycloalkyl-l-carbonsäure.     Das Verfahren ist dadurch gekennzeichnet,  dass man     einen    reaktionsfähigen Ester des       Piperidinoäthanols    auf     eine    Verbindung der  Formel  
EMI0001.0008     
    worin X einen bei der Reaktion sich abspal  tenden Rest bedeutet, einwirken lässt. Als  Verbindungen der obigen Formel können bei  spielsweise verwendet werden die freie Säure  und ihre Salze.  



  Die erhaltene neue Verbindung, der       1-Phenyl-cyclopentan-l-carbonsäure-        (,B-pipe-          ridino-äthyl)-ester,    bildet eine farblose Flüs  sigkeit vom Siedepunkt     135-136     unter  0,15 mm. Die Verbindung soll therapeutische  Verwendung     finden.     



  <I>Beispiel:</I>  19 Teile     1-Phenyl-cyclopentyl-l-carbon-          säure    werden mit 14,8 Teilen     Piperidino-          äthylchlorid    und 14 Teilen Pottasche in  250 Teilen trockenem Essigester 12 Stunden  unter Rühren zum Sieden erhitzt. Nach dem  Erkalten     nutscht    man ab, wäscht mit Essig  ester nach und     schüttelt    die vereinigten       Essigesterlösungen        mit        verdünnter    Salz  säure aus.

   Die saure, wässerige Lösung wird         ausgeäthert,    die Base     mit    Pottasche in Frei  heit gesetzt und in Äther     aufgenommen.    Die       ätherische    Lösung wird mit     Wasser    gewa  schen, über Pottasche getrocknet und das Lö  sungsmittel     abdestilliert.    Der     basische    Ester  siedet unter 0,15 mm bei 135-136 .  



  An Stelle von Pottasche kann auch     ein     anderes     Alkalicarbonat        verwendet    werden,  oder man     kann    z. B. auch direkt ein Metall  salz der     1-Phenyl-cyclopentan-l-carbonsäure     mit     Piperidinoäthylchlorid    oder einem Salz  desselben umsetzen.  



  Zum gleichen Endprodukt gelangt man  auch durch Erhitzen von     1-Phenyl-cyclo-          pentan-l-carbonsäure    mit     Piperidinoäthyl-          chlorid        in    An- oder Abwesenheit eines Lö  sungsmittels.  



  Statt des     Chlorwasserstoffesters    können  auch Ester des     Piperidinoäthanols    mit andern       Halogenwasserstoffsäuren    oder z. B. mit       Arylsulfonsäuren,    wie mit     p-Toluolsulfo-          säure,        verwendet    werden.



      Process for the preparation of a basic ester of a 1 aryl-cycloalkyl-1-carboxylic acid. The present patent is a process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The process is characterized in that a reactive ester of piperidinoethanol is used on a compound of the formula
EMI0001.0008
    where X is a residue that splits off during the reaction, can act. The free acid and its salts can be used, for example, as compounds of the above formula.



  The new compound obtained, the 1-phenyl-cyclopentane-1-carboxylic acid (, B-piperidino-ethyl) ester, forms a colorless liquid with a boiling point of 135-136 below 0.15 mm. The compound is intended to find therapeutic use.



  <I> Example: </I> 19 parts of 1-phenyl-cyclopentyl-1-carboxylic acid are heated to boiling with stirring for 12 hours with 14.8 parts of piperidinoethyl chloride and 14 parts of potash in 250 parts of dry ethyl acetate. After cooling, it is filtered off with suction, washed with ethyl acetate and the combined ethyl acetate solutions are shaken out with dilute hydrochloric acid.

   The acidic, aqueous solution is extracted with ether, the base is set free with potash and taken up in ether. The ethereal solution is washed with water, dried over potash and the solvent is distilled off. The basic ester boils below 0.15 mm at 135-136.



  Instead of potash, another alkali metal carbonate can be used, or z. B. also directly implement a metal salt of 1-phenyl-cyclopentane-l-carboxylic acid with piperidinoethyl chloride or a salt thereof.



  The same end product can also be obtained by heating 1-phenyl-cyclopentane-1-carboxylic acid with piperidinoethyl chloride in the presence or absence of a solvent.



  Instead of the hydrogen chloride ester of piperidinoethanol with other hydrohalic acids or z. B. with arylsulfonic acids, such as with p-toluenesulfonic acid, can be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Esters einer 1-Aryl-cycloalkyl-l-carbonsäure, dadurch gekennzeichnet, dass man einen reak tionsfähigen Ester des Piperidinoäthanols auf eine Verbindung der Formel EMI0001.0051 worin X einen bei der Reaktion sich abspal tenden Rest bedeutet, einwirken lässt. Die erhaltene neue Verbindung, der 1-Phenyl-cyclopentan-l-carbonsäure-(ss-pipe- ridino-äthyl)-ester, bildet eine farblose Flüs sigkeit vom Siedepunkt 1ä5-136 unter 0,15 mm. UNTERANSPRüCHE: 1. Claim: Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid, characterized in that a reactive ester of piperidinoethanol is used on a compound of the formula EMI0001.0051 where X is a residue that splits off during the reaction, can act. The new compound obtained, the 1-phenyl-cyclopentane-1-carboxylic acid (ss-piperidino-ethyl) ester, forms a colorless liquid with a boiling point of 1-5-136 below 0.15 mm. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man einen reak tionsfähigen Ester des Piperidinoäthanols auf 1-Phenyl-cyclopentan-l-ear bonsäure einwir ken lässt. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man einen reak tionsfähigen Ester des Piperidinoäthanols auf ein Metallsalz der 1-Phenyl-cyclopentan-l- carbonsäure einwirken lässt. 3. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als reak tionsfähigen Ester des Piperidinoäthanols einen Halogenwasserstoffsäureester verwen det. Process according to patent claim, characterized in that a reactive ester of piperidinoethanol is allowed to act on 1-phenyl-cyclopentane-1-acidic acid. 2. The method according to claim, characterized in that a reactive ester of piperidinoethanol is allowed to act on a metal salt of 1-phenyl-cyclopentane-1-carboxylic acid. 3. The method according to claim, characterized in that a hydrohalic acid ester is used as the reactive ester of piperidinoethanol.
CH247927D 1944-03-20 1944-03-20 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. CH247927A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH234452T 1944-03-20
CH247927T 1944-03-20

Publications (1)

Publication Number Publication Date
CH247927A true CH247927A (en) 1947-03-31

Family

ID=25727879

Family Applications (1)

Application Number Title Priority Date Filing Date
CH247927D CH247927A (en) 1944-03-20 1944-03-20 Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH247927A (en)

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