CH99208A - Process for the preparation of the tropic acid ester of piperidyloxyethylamine. - Google Patents

Process for the preparation of the tropic acid ester of piperidyloxyethylamine.

Info

Publication number
CH99208A
CH99208A CH99208DA CH99208A CH 99208 A CH99208 A CH 99208A CH 99208D A CH99208D A CH 99208DA CH 99208 A CH99208 A CH 99208A
Authority
CH
Switzerland
Prior art keywords
piperidyloxyethylamine
tropic acid
acid ester
preparation
tropic
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ch Grenzach
Original Assignee
Chemische Werke Grenzach Aktie
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 Chemische Werke Grenzach Aktie filed Critical Chemische Werke Grenzach Aktie
Publication of CH99208A publication Critical patent/CH99208A/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)
  • Plural Heterocyclic Compounds (AREA)

Description

  

  Verfahren zur Darstellung des     Tropasäureesters    des     Piperidyloxyäthylamins.       Die     Esterifizierung    des     Hydroxyls    in  einem     Alkamin    mit     Hilfe    der     Tropasäure    ist  bisher nur bei einigen wenigen und dazu noch  recht kompliziert .gebauten      xybasen    durch  beführt worden;

   ausser beim     Tropin    zum Bei  spiel noch bei einigen dem     Tropin    in der  Struktur nahestehenden     bicyklischen    Verbin  dungen (Deutsche Patentschriften 151189,  157698 und Berichte der Deutschen Chemi  schen Gesellschaft, Band 51, 1918, Seite 285  und     Band    53, 192.0, Seite 601).

       Tropasäure-          ester    von     Alkaminen,    die kein     Ringsystem          vomTropantypus    enthalten und     dieHydroxyl-          gruppe    in einer offenen Kette tragen, sind  bisher nicht     bekannt        geworden.    Nun zeigte  sich, dass die Angliederung des     Tropylrestes          ,in    solche     Alkamine    in überraschend leichter       Weise    gelingt, und     -dass-    die neuen Körper       Eigenschaften    aufweisen,

   welche sie befähi  gen, das bisher technisch     immer    noch nur aus  ,der Pflanze     gewinnbare        Atropin    zu ersetzen.       Unter,den        Alkaminen,    die kein Ringsystem  vom     Tropantypus    enthalten und das     Hydroxyl     in einer offenen Kette tragen, zeigten sich  aber nur diejenigen, welche die Hydroxyl-    Kruppe in -Stellung     zum.Sti-ckstoffatom    ent  halten, als besonders stark     wirksam    und zur  therapeutischen Verwertung geeignet.  



  Gegenstand der vorliegenden Erfindung  ist ein Verfahren zur Darstellung des     Tropa-          säureesters    des     Piperidyloxyäthylamins,    wel  ches darin besteht,     @dass    man     Piperidyloxy-          äthylamin    mit     Tropasäure        h.alogenid        ver-          estert.     



  Der     Tropasäureester    des     Piperidyloxy-          äthylamins    ist ein 01. Auch das Chlorhydrat  scheidet sich ölig     aus.    Es ist in Wasser leicht  löslich und in     wässeriger    Lösung völlig halt  bar. Der Ester soll     therapeutische    V     erwen-          -dung    finden.  



  <I>Beispiel:</I>  10 Teile salzsaures     Piperidyloxyäthyl-          amin    werden mit der aus 10 Teilen     Tropa-          säure    nach den Angaben von     Wolffenstein     und     Hamlock    (Berichte der Deutschen Che  mischen Gesellschaft, Band 41, 1918, Seite  728)     bereitetenMengeAzetyltropasäurachlorid     versetzt, 30 Minuten auf dem Wasserbad er  wärmt und dann 12     Stunden    in der     gälte     stehen gelassen.

   Das dickflüssige Reaktions-           proIukt    wird mit 80     \feilen    Wasser über  gossen und die gebildete Lösung längere Zeit  in, der Kälte sich selbst überlassen. Dabei  wird     fler    zunächst     entstandene        Azethyltropa-          säureester    verseift.

       Flernap-h    wird mit Na  tronlauge nahezu neutralisiert, eine     1O         "o-ige          Kaliumkarbonatlösung    zugesetzt und der ab  geschiedene     Tro-pasäureester    des     Piperidyl-          oxyäthylamins    in Äther aufgenommen. Die       ätherische    Lösung wird mit     I%aliumka.rbonat     getrocknet. Das mit ätherischer Salzsäure  ausgefällte Chlorhydrat scheidet sich .als farb  loses<B>01</B> ab. Der ,aus dem Chlorhydrat ge  wonnene Ester     ist    ebenfalls ölig.



  Process for the preparation of the tropic acid ester of piperidyloxyethylamine. The esterification of the hydroxyl in an alkamine with the help of tropic acid has so far only been carried out in a few and also quite complicated xybases;

   except for tropine, for example, some bicyclic compounds with a similar structure to tropine (German patents 151189, 157698 and reports of the German Chemical Society, volume 51, 1918, page 285 and volume 53, 192.0, page 601).

       Tropic acid esters of alkamines which do not contain a ring system of the tropane type and which carry the hydroxyl group in an open chain have not become known to date. It has now been shown that the tropyl radical can be incorporated into such alkamines in a surprisingly easy manner, and that the new body has properties,

   which enable them to replace the atropine that was previously only obtained from the plant. Among the alkamines that do not contain a tropane-type ring system and carry the hydroxyl in an open chain, however, only those that contain the hydroxyl croup in the position of the nitrogen atom have been shown to be particularly effective and for therapeutic use suitable.



  The present invention relates to a process for the preparation of the tropic acid ester of piperidyloxyethylamine, which consists in esterifying piperidyloxyethylamine with tropic acid h.alogenide.



  The tropic acid ester of piperidyloxyethylamine is an 01. The chlorohydrate also precipitates in an oily form. It is easily soluble in water and completely stable in aqueous solution. The ester is said to be of therapeutic use.



  <I> Example: </I> 10 parts of hydrochloric acid piperidyloxyethylamine are mixed with the amount of acetyl tropic acid chloride prepared from 10 parts of tropic acid according to the information from Wolffenstein and Hamlock (reports of the German Chemical Society, Volume 41, 1918, page 728), He warms up on the water bath for 30 minutes and then leaves it to stand in the cold for 12 hours.

   The viscous reaction product is poured over 80 parts of water and the solution formed is left to stand in the cold for a long time. In the process, the acetyl tropic acid ester initially formed is saponified.

       Flernap-h is almost neutralized with sodium hydroxide solution, a 10% strength potassium carbonate solution is added and the precipitated trophic acid ester of piperidyl oxyethylamine is taken up in ether. The ethereal solution is dried with 1% aluminum carbonate. The precipitated with ethereal hydrochloric acid Chlorohydrate separates out as a colorless <B> 01 </B>. The ester obtained from the chlorohydrate is also oily.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung des Tropa- säureesters des Pipeiidyloxyäthylamins, da- ,durch gekennzeichnet, dass man Piperidyl- oxyäthylamin mit Tropasäure halogenid v er- Der Der Tropasä.ureester des Piperidyloxy- äthylamins ist ein<B>01.</B> Auch das Chlorhydrat scheidet sich ölig aus. <B> PATENT CLAIM: </B> Process for the preparation of the tropic acid ester of pipeiidyloxyethylamine, characterized in that piperidyloxyethylamine is halide with tropic acid. The tropic acid ester of piperidyloxyethylamine is a <B> 01. </B> The chlorohydrate also excretes in an oily form. Es ist in Wasser leicht löslich und in wässeriger Lösung völlig halt bar. Der Ester --all therapeutische Verwen dung finden. It is easily soluble in water and completely stable in aqueous solution. The ester - all therapeutic uses.
CH99208D 1922-04-12 1922-04-12 Process for the preparation of the tropic acid ester of piperidyloxyethylamine. CH99208A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH99208T 1922-04-12
CH98917T 1922-04-12

Publications (1)

Publication Number Publication Date
CH99208A true CH99208A (en) 1923-05-16

Family

ID=25705474

Family Applications (1)

Application Number Title Priority Date Filing Date
CH99208D CH99208A (en) 1922-04-12 1922-04-12 Process for the preparation of the tropic acid ester of piperidyloxyethylamine.

Country Status (1)

Country Link
CH (1) CH99208A (en)

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