CH220972A - Process for the preparation of a basic ester. - Google Patents

Process for the preparation of a basic ester.

Info

Publication number
CH220972A
CH220972A CH220972DA CH220972A CH 220972 A CH220972 A CH 220972A CH 220972D A CH220972D A CH 220972DA CH 220972 A CH220972 A CH 220972A
Authority
CH
Switzerland
Prior art keywords
sep
ester
piperidinoethanol
marked
acid
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH220972A publication Critical patent/CH220972A/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

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

Description

  

  Verfahren zur Darstellung eines     basischen        .Esters.       Es wurde gefunden, dass man zu einem  basischen Ester gelangen kann, wenn man  auf eine Verbindung der Formel:  
EMI0001.0003     
    worin X einen bei der Reaktion sich abspal  tenden     Rest    bedeutet, einen reaktionsfähigen  Ester des     Piperidinoäthanols    einwirken lässt.  



  Der so erhaltene     Phenyl-cyclohexyl-essig-          säure-piperidinoäthanolester    bildet ein<B>01</B>  vom     Kp        o",    180-182  . Sein Hydrochlorid  schmilzt bei 166-167  .  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



  <I>Beispiel:</I>  22 Teile     Phenyl-cyclohexyl-essigsäure,     19 Teile     Chloräthyl-piperidin-hydrochlorid       und 35 Teile     Kaliumkarbonat    werden in  300 Teilen Aceton 24 Stunden auf dem  Wasserbade     erwärmt.    Hierauf wird     abfil-          triert,    die Lösung eingedampft und der Ein  dampfrückstand in Äther gelöst. Die äthe  rische Lösung wird mit Wasser gewaschen,  über     Kaliumkarbonat    getrocknet und. ver  dampft.

   Durch Destillation des Rückstandes  gewinnt man den     Phenyl-cyclohexyl-essig-          säure-piperidinoäthanolester    vom     Kp        ",l,    180  bis 182   in nahezu quantitativer Ausbeute.  



  An Stelle von Aceton kann auch ein  anderes indifferentes Lösungsmittel verwen  det werden.  



  Dieselbe Verbindung kann auch gewonnen  werden, wenn man z. B. an Stelle von       Kaliumkarbonat    ein anderes     Alkalikarbonat     verwendet, oder wenn man ein fertiges Al  kali- oder anderes Metallsalz der     Phenyl-          cyclohexyl-essigsäure    mit     Chloräthyl-piperi-          din    umsetzt.  



  Denselben Endstoff erhält man ferner  z. B. auch durch Umsetzung von     Phenyl-    .    
EMI0002.0001     
  
    oyelohexyl-essibsäure <SEP> mit <SEP> Chloräthy <SEP> 1-piperi  din <SEP> in <SEP> Gegenwart <SEP> eines <SEP> indifferenten <SEP> Lii  sunbsmittels <SEP> wie <SEP> z. <SEP> B. <SEP> Isopropylalkohol.
<tb>  Statt <SEP> des <SEP> Salzsäureesters <SEP> li#iiniien <SEP> auch
<tb>  Ester <SEP> des <SEP> Piperidinoäthanols <SEP> mit <SEP> andern
<tb>  Halobenwasserstoffsäuren <SEP> oder <SEP> z. <SEP> B. <SEP> mil
<tb>  3rylsulfonsäuren, <SEP> wie <SEP> Toluolsulfonsälire,
<tb>  verwendet <SEP> erden.



  Method for the representation of a basic .ester. It has been found that a basic ester can be obtained by using a compound of the formula:
EMI0001.0003
    wherein X is a residue that splits off in the reaction, a reactive ester of piperidinoethanol can act.



  The phenyl-cyclohexyl-acetic acid-piperidinoethanol ester thus obtained forms a 01 with a range of 180-182. Its hydrochloride melts at 166-167.



  The new compound should find therapeutic use.



  <I> Example: </I> 22 parts of phenyl-cyclohexyl-acetic acid, 19 parts of chloroethylpiperidine hydrochloride and 35 parts of potassium carbonate are heated in 300 parts of acetone on a water bath for 24 hours. It is then filtered off, the solution is evaporated and the residue is dissolved in ether. The ethereal solution is washed with water, dried over potassium carbonate and. evaporates.

   By distilling the residue, the phenyl-cyclohexyl-acetic acid-piperidinoethanol ester of boiling point 1.180 to 182 is obtained in almost quantitative yield.



  Instead of acetone, another inert solvent can also be used.



  The same connection can also be obtained by z. B. used instead of potassium carbonate, another alkali metal carbonate, or if you react a finished alkali or other metal salt of phenyl cyclohexyl acetic acid with chloroethyl piperidine.



  The same end product is also obtained, for. B. also by reaction of phenyl.
EMI0002.0001
  
    oyelohexyl-esibic acid <SEP> with <SEP> chloroethy <SEP> 1-piperidine <SEP> in <SEP> presence <SEP> of a <SEP> indifferent <SEP> Li-sun medium <SEP> like <SEP> e.g. <SEP> B. <SEP> isopropyl alcohol.
<tb> Instead of <SEP> the <SEP> hydrochloric acid ester <SEP> li # iiniien <SEP> also
Change <tb> ester <SEP> of <SEP> piperidinoethanol <SEP> with <SEP>
<tb> Hydrogen halide acids <SEP> or <SEP> e.g. <SEP> B. <SEP> mil
<tb> 3rylsulfonic acids, <SEP> like <SEP> toluenesulfonic acids,
<tb> uses <SEP> ground.

Claims (1)

EMI0002.0002 PATENTANSPRUCH: <tb> Verfahren <SEP> zur <SEP> Herstellung <SEP> eines <SEP> basischen <tb> Esters, <SEP> dadurch <SEP> bel,:eunzeichnet. <SEP> dass <SEP> nian <SEP> auf <tb> eine <SEP> Verbindung; <SEP> der <SEP> Formel: EMI0002.0003 EMI0002.0004 worin <SEP> X <SEP> einen <SEP> bei <SEP> der <SEP> Reaktion <SEP> sich <SEP> abspal tenden <SEP> Rest <SEP> bedeutet, <SEP> einen <SEP> reaktionsfähigen <tb> Ester <SEP> des <SEP> Piperidinoäthanols <SEP> einwirken <SEP> lässt. <tb> Der <SEP> so <SEP> erhaltene <SEP> Phenyl-cyelohexyl-essib säure-piperidinoäthanolester <SEP> bildet <SEP> ein <SEP> (l <SEP> vom <tb> KP <SEP> ",i5 <SEP> 18Q-18? <SEP> ". EMI0002.0002 PATENT CLAIM: <tb> Method <SEP> for the <SEP> production <SEP> of a <SEP> basic <tb> Esters, <SEP> thereby <SEP> bel,: eunmarked. <SEP> that <SEP> nian <SEP> on <tb> a <SEP> connection; <SEP> of the <SEP> formula: EMI0002.0003 EMI0002.0004 where <SEP> X <SEP> means a <SEP> at <SEP> the <SEP> reaction <SEP> <SEP> separating <SEP> remainder <SEP>, <SEP> means a <SEP> reactive <tb> Ester <SEP> of <SEP> piperidinoethanol <SEP> allows <SEP> to act. <tb> The <SEP> so <SEP> obtained <SEP> phenyl-cyelohexyl-essib acid-piperidinoethanol ester <SEP> forms <SEP> a <SEP> (l <SEP> from <tb> KP <SEP> ", i5 <SEP> 18Q-18? <SEP>". <SEP> Sein <SEP> Hydroelilorid <SEP> schmilzt <tb> bei <SEP> 166-167 <SEP> . <tb> Die <SEP> neue <SEP> Verbindung <SEP> soll <SEP> tlif@rapeutische <tb> V <SEP> erwendunb <SEP> finden. EMI0002.0005 UNTERANSPRÜCHE: <tb> 1. <SEP> Verfahren <SEP> naeli <SEP> Patentanspruch, <SEP> da durch <SEP> 'gekennzeichnet, <SEP> dass <SEP> man <SEP> auf <SEP> Phen <SEP> S:l c@-cloliexyl-essib,äure <SEP> einen <SEP> reaktionsfäliiben <tb> later <SEP> des <SEP> I'iper <SEP> idinoüthanols <SEP> einwirken <SEP> lässt. <tb> ?. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> da diuch <SEP> 'gekennzeichnet, <SEP> dass <SEP> inan <SEP> auf <SEP> ein <tb> Helallsalz <SEP> der <SEP> Pheiiyl-cyelohe_Kyl-essigsäure <tb> einen <SEP> reaktioti: <SEP> His <SEP> hydroeliloride <SEP> is melting <tb> at <SEP> 166-167 <SEP>. <tb> The <SEP> new <SEP> connection <SEP> should <SEP> tlif @ rapeutische <tb> V <SEP> find use <SEP>. EMI0002.0005 SUBCLAIMS: <tb> 1. <SEP> method <SEP> naeli <SEP> patent claim, <SEP> as marked by <SEP> ', <SEP> that <SEP> man <SEP> on <SEP> Phen <SEP> S: lc @ -cloliexyl-essib, acid <SEP> a <SEP> reactive <tb> later <SEP> of the <SEP> I'iper <SEP> idinoüthanol <SEP> allows <SEP> to act. <tb>?. <SEP> method <SEP> according to <SEP> patent claim, <SEP> because it is marked with <SEP> ', <SEP> that <SEP> inan <SEP> on <SEP> <tb> Helallalz <SEP> of <SEP> Pheiiyl-cyelohe_Kyl-acetic acid <tb> a <SEP> reactioti: sfähigen <SEP> Ester <SEP> des <SEP> Piperidino äthanols <SEP> einwirken <SEP> lässt. <tb> 3. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> da z@ureh <SEP> 'gekennzeichnet, <SEP> dass <SEP> man <SEP> als <SEP> reaktions fähigeii <SEP> Ester <SEP> des <SEP> Piperidirioäthanols <SEP> einen <tb> Ha@o@,@eiiwas,cr,toff@üureester <SEP> des <SEP> Piperidino üthanols <SEP> verv-endet. <tb> d. <SEP> Verfahren <SEP> nach <SEP> Patentansprueli <SEP> und <tb> Unteranspruch. <SEP> 3, <SEP> dadurch <SEP> 'gekennzeichnet, <tb> da13 <SEP> mazi <SEP> den <SEP> Salzsäureester <SEP> des <SEP> Piperidino :il-hanols <SEP> verwendet. <tb> i. <SEP> Vei: capable <SEP> ester <SEP> of <SEP> piperidino ethanol <SEP> allows <SEP> to act. <tb> 3. <SEP> method <SEP> according to <SEP> patent claim, <SEP> because z @ ureh <SEP> 'marked, <SEP> that <SEP> one <SEP> as <SEP> capable of reacting <SEP > Ester <SEP> of <SEP> piperidirioethanol <SEP> one <tb> Ha @ o @, @ eiiwas, cr, toff @ üureester <SEP> of the <SEP> Piperidino üthanol <SEP> ends. <tb> d. <SEP> procedure <SEP> according to <SEP> patent claims <SEP> and <tb> subclaim. <SEP> 3, <SEP> marked with <SEP> ', <tb> da13 <SEP> mazi <SEP> the <SEP> hydrochloric acid ester <SEP> of the <SEP> piperidino: il-hanols <SEP> is used. <tb> i. <SEP> Vei: .-fahren. <SEP> nach <SEP> Patentanspruch, <SEP> da durch <SEP> "#elzennzeichnet. <SEP> dass <SEP> man <SEP> als <SEP> reaktions fiihiben <SEP> Ester <SEP> des <SEP> Piperidinoäthanols <SEP> einen <tb> -\-rylsulfonsäiirec,ster <SEP> des <SEP> Piperidinoäthanols <tb> verwendet. <tb> Fi. <SEP> VerFaliren <SEP> nach <SEP> Patentanspruch <SEP> und <tb> L'nteran-slirncli <SEP> a, <SEP> dadurch <SEP> gekennzeichnet, <tb> rhiss <SEP> inan <SEP> einen <SEP> Toluolsulfonsäureester <SEP> des <tb> Pilierirlinoiithanols <SEP> verwendet. .-drive. <SEP> according to <SEP> patent claim, <SEP> because it is identified by <SEP> "#elz. <SEP> that <SEP> is <SEP> as a <SEP> reaction <SEP> ester <SEP> of <SEP> piperidinoethanol <SEP> one <tb> - \ - rylsulfonsäiirec, ster <SEP> of <SEP> piperidinoethanol <tb> used. <tb> Fi. <SEP> VerFaliren <SEP> according to <SEP> patent claim <SEP> and <tb> L'nteran-slirncli <SEP> a, <SEP> characterized by <SEP>, <tb> rhiss <SEP> inan <SEP> a <SEP> toluenesulfonic acid ester <SEP> des <tb> Pilierirlinoiithanols <SEP> used.
CH220972D 1938-08-05 1938-08-05 Process for the preparation of a basic ester. CH220972A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH220972T 1938-08-05
CH532943X 1938-08-05

Publications (1)

Publication Number Publication Date
CH220972A true CH220972A (en) 1942-04-30

Family

ID=25726509

Family Applications (1)

Application Number Title Priority Date Filing Date
CH220972D CH220972A (en) 1938-08-05 1938-08-05 Process for the preparation of a basic ester.

Country Status (1)

Country Link
CH (1) CH220972A (en)

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