CH296267A - Process for the preparation of the piperidinoethyl ester of 4-amino-2-oxy-benzoic acid. - Google Patents

Process for the preparation of the piperidinoethyl ester of 4-amino-2-oxy-benzoic acid.

Info

Publication number
CH296267A
CH296267A CH296267DA CH296267A CH 296267 A CH296267 A CH 296267A CH 296267D A CH296267D A CH 296267DA CH 296267 A CH296267 A CH 296267A
Authority
CH
Switzerland
Prior art keywords
sep
oxy
amino
benzoic acid
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Rheinpreussen Aktienges Chemie
Original Assignee
Rheinpreussen Ag
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 Rheinpreussen Ag filed Critical Rheinpreussen Ag
Publication of CH296267A publication Critical patent/CH296267A/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Description

  

  Verfahren zur Herstellung des     Piperidinoäthylesters    der     4-Amino-2.oxy-benzoesäure.     
EMI0001.0003     
  
    Gegenstand <SEP> des <SEP> vorliegenden <SEP> Patentes <SEP> ist
<tb>  ein <SEP> Verfahren <SEP> zur <SEP> Herstellung <SEP> des <SEP> Piperidino  iithylestcr:s <SEP> der <SEP> 4-Amino-2-oxy <SEP> -benzoesä-Lire,
<tb>   elches <SEP> dadureb, <SEP> gekennzeichnet <SEP> ist, <SEP> dass <SEP> man
<tb>  ciii <SEP> Salz <SEP> der <SEP> 4.-Amino-2-oxy-lienzoesäure <SEP> mit.
<tb>  einem. <SEP> P-Piperidino-äthylhalogenid, <SEP> wie <SEP> z. <SEP> B.
<tb>  I'iperidinoäthylelilorid, <SEP> umsetzt. <SEP> Als <SEP> Salze <SEP> der
<tb>  ;Yellannten <SEP> Säure <SEP> eignen, <SEP> sieh <SEP> besonders <SEP> die
<tb>  -111zziliniet.ill- <SEP> sowie <SEP> die <SEP> Erdalkalimetallsalze.

         <I>Beispiel:</I>  <B>30</B>     @--        Natriumsalz    der     4-Ainino-2-oxy-ben-          zoesäure        (wasserfrei)    werden in 300     ein-'        ab-          Solutein        Äthanol    gegeben und das Gemisch       >rinn    Sieden erhitzt.

   Sodann trägt man     trop-          !'enweise    im Verlaufe von 2     Stunden        unter          Rühren    die Lösung     von        2-1    g     I.-Chlor-2-N-pi-          I>ei#icIino-äthan    in 50     ein'    absolutem     Äthanol     ein und erhitzt weitere 6 Stunden zum Sie  den.

   lach dem Filtrieren wird die     alkoho-          lisehe    Lösung     eingedampft    und der ölige       Rückstand    mit verdünnter     Salzsäure    verrührt.  f     >as        @-ebildete    Hydrochlorid des     P-N-Piperi-          dino-kliyIesters    der     4-Amiiio-2-oxy-benzoe-          siiure    wird zur Reinigung aus Wasser umkri  stallisiert. Schmelzpunkt 227  (Zersetzung).

           Die        Ausbeute        beträgt        40,1        g        (80%        der        Theo-          rie).     



  Das     llonochlorhydrat    des     Endstoffes    soll  für therapeutische Zwecke verwendet werden.  Dieser Ester weist eine starke     anästhetische     Wirkung auf und übertrifft in dieser Hin  sieht sogar erheblich den     Diäthylaminoäthyl-          ester    der     p-Amino-benzoesätire.  



  Process for the preparation of the piperidinoethyl ester of 4-amino-2.oxy-benzoic acid.
EMI0001.0003
  
    The subject of <SEP> of the <SEP> present <SEP> patent <SEP> is
<tb> a <SEP> process <SEP> for the <SEP> production <SEP> of the <SEP> Piperidino iithylestcr: s <SEP> the <SEP> 4-Amino-2-oxy <SEP> -benzoesä-Lire,
<tb> elches <SEP> dadureb, <SEP> is marked <SEP>, <SEP> that <SEP> man
<tb> ciii <SEP> Salt <SEP> of <SEP> 4.-Amino-2-oxy-lienoic acid <SEP> with.
<tb> one. <SEP> P-piperidino-ethyl halide, <SEP> like <SEP> e.g. <SEP> B.
<tb> I'iperidinoethylelilorid, <SEP> converts. <SEP> As <SEP> salts <SEP> the
<tb>; Yellennen <SEP> acid <SEP> are suitable, <SEP> see <SEP> especially <SEP> those
<tb> -111zziliniet.ill- <SEP> and <SEP> the <SEP> alkaline earth metal salts.

         <I> Example: </I> <B> 30 </B> @ - the sodium salt of 4-ainino-2-oxy-benzoic acid (anhydrous) are added to 300 one-solute ethanol and the mixture > rinn boiling heated.

   The solution of 2-1 g of 1-chloro-2-N-pi-Ii-icino-ethane in 50% of an absolute ethanol is then added dropwise over the course of 2 hours with stirring, and more is heated 6 hours to you.

   After filtering, the alcoholic solution is evaporated and the oily residue is stirred with dilute hydrochloric acid. For purification, the hydrochloride of the P-N-piperidino-kliyIester of 4-amino-2-oxy-benzoic acid is recrystallized from water. Melting point 227 (decomposition).

           The yield is 40.1 g (80% of theory).



  The ionochlorohydrate of the end product should be used for therapeutic purposes. This ester has a strong anesthetic effect and in this respect even considerably exceeds the diethylaminoethyl ester of p-amino-benzoate.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des Piperidino- äthylesters der 4-Amino-2-oxy -benzoesäure, dadurch gekennzeichnet, dass man ein Salz der 4.-Amino-2-oxy-benzoesäure mit einem P-Pi- peridino-äthy lhalogenid umsetzt. Der erhaltene 4-Amino-2-oxy-benzoesätire- piperidinoäthylester stellt eine kristalline Substanz dar, die in verdünnter Säure leicht löslich ist. PATENT CLAIM: A process for the preparation of the piperidino ethyl ester of 4-amino-2-oxy-benzoic acid, characterized in that a salt of 4-amino-2-oxy-benzoic acid is reacted with a p-p-peridino-ethyl halide. The 4-amino-2-oxy-benzoesätire- piperidinoäthylester is a crystalline substance which is easily soluble in dilute acid. Der Ester bildet ein Monohydrat in Form weisser Kristalle vom Schmelzpunkt 73 , während die wasserfreie Verbindung bei 68 schmilzt. Das Monochlorhydrat des Esters erhält man in Form weisser Kristalle vom Schmelzpunkt<B>2270</B> (Zersetzung), die in Was ser leicht löslich sind. The ester forms a monohydrate in the form of white crystals with a melting point of 73, while the anhydrous compound melts at 68. The monochlorohydrate of the ester is obtained in the form of white crystals with a melting point of <B> 2270 </B> (decomposition), which are easily soluble in water.
CH296267D 1949-10-22 1950-10-26 Process for the preparation of the piperidinoethyl ester of 4-amino-2-oxy-benzoic acid. CH296267A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE289538X 1949-10-22
DE296267X 1950-07-31

Publications (1)

Publication Number Publication Date
CH296267A true CH296267A (en) 1954-01-31

Family

ID=32870132

Family Applications (2)

Application Number Title Priority Date Filing Date
CH289538D CH289538A (en) 1949-10-22 1950-03-14 Process for the preparation of the diethylaminoethyl ester of 4-amino-2-oxy-benzoic acid.
CH296267D CH296267A (en) 1949-10-22 1950-10-26 Process for the preparation of the piperidinoethyl ester of 4-amino-2-oxy-benzoic acid.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH289538D CH289538A (en) 1949-10-22 1950-03-14 Process for the preparation of the diethylaminoethyl ester of 4-amino-2-oxy-benzoic acid.

Country Status (1)

Country Link
CH (2) CH289538A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0953800A1 (en) * 1998-04-29 1999-11-03 Johannes Mag. Huter Apparatus for controlling the light emitted by an elongated light source

Also Published As

Publication number Publication date
CH289538A (en) 1953-03-15

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