CH316618A - Process for the preparation of a previously unknown acid amide-like piperidine derivative - Google Patents

Process for the preparation of a previously unknown acid amide-like piperidine derivative

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Publication number
CH316618A
CH316618A CH316618DA CH316618A CH 316618 A CH316618 A CH 316618A CH 316618D A CH316618D A CH 316618DA CH 316618 A CH316618 A CH 316618A
Authority
CH
Switzerland
Prior art keywords
sep
acid amide
previously unknown
preparation
piperidine
Prior art date
Application number
Other languages
German (de)
Inventor
Stoll Arthur Dr Prof
Pierre Dr Bourquin Jean
Original Assignee
Sandoz 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 Sandoz Ag filed Critical Sandoz Ag
Publication of CH316618A publication Critical patent/CH316618A/en

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  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines bisher unbekannten     säureamidartigen        Piperidinderivates       Es wurde befunden, dass man zum bisher unbekannten     1-Metliyl-l-(p-äthoxy-benzoyl-          amino)-piperidin    der folgenden Formel  
EMI0001.0005     
  
EMI0001.0006     
  
    gelangt, <SEP> indem <SEP> man <SEP> auf <SEP> 1-Methyl-l-aniino  piperidin <SEP> p-iithoxy-benzoylehlorid <SEP> einwirken
<tb>  lässt.
<tb>  



  <I>Beispiel</I>
<tb>  Zu <SEP> einer <SEP> Lösung <SEP> von <SEP> 63,0 <SEP> g <SEP> p-,#,tlioxy-ben  zoylchlorid <SEP> (1 <SEP> Mol <SEP> + <SEP> 10 <SEP> 0/a <SEP> Überschuss) <SEP> in
<tb>  150 <SEP> em3 <SEP> Benzol. <SEP> wird <SEP> bei <SEP> Zimmertemperatur
<tb>  eine <SEP> Lösung <SEP> von <SEP> 35,0 <SEP> g <SEP> 1-Methyl-4-amino-pipe  ridin <SEP> (l. <SEP> 1o1) <SEP> in <SEP> 150 <SEP> em3 <SEP> Benzol <SEP> zugetropft.       Man lässt über Nacht stehen und kocht noch  1 Stunde am     Pücldluss.    Die     Benzollösun-    wird  n     iit    dem Niederschlag mit 300     cin3    1,5-n.

   Salz  säure     ausgeschüttelt,    der     wässerige        Auszug     mit     3-l1.    Natronlauge     phenolphtalein-alka.liseh     bestellt und die     alis-efallene    Base, das     1-Me-          thyl-4-(p-äthoxy-benzoylamiiio)-piperidin,    ab  genutscht. und aus der achtfachen Menge  Aceton umkristallisiert.     Smp.    182-181 .

    
EMI0001.0020     
  
    C15112202N2 <SEP> Ber. <SEP> C <SEP> 68,67 <SEP> 118,45 <SEP> N <SEP> 10,68 <SEP> %
<tb>  <B>GU</B> <SEP> ef. <SEP> 68,61 <SEP> 9,08 <SEP> 10,841/o       Wird das     Säureamid    in der     äquivalenten     Menge     1-n.    Salzsäure gelöst, die Lösung im  Vakuum bei 50  zur Trockne     eingeengt,    der  Rückstand in der vierfachen Menge     abs.    Al  kohol kochend gelöst und die     Lösllllg    mit der    zwei-     bis    dreifachen Menge     Ather    versetzt,

   so  fällt das     1-Iydroelilorid    des     1.-Methyl.-1-(p-          äthoxy    -     benzoylamino)    -     piperidins    kristallin  aus.     Smp.    213-216 .  
EMI0001.0035     
  
    C15112202N2 <SEP> - <SEP> HC1 <SEP> - <SEP> H20 <SEP> Bei'. <SEP> C <SEP> 56,86 <SEP> 117,95 <SEP> N <SEP> 8,81 <SEP> 0/a
<tb>  Ctef. <SEP> 56,17 <SEP> 8,07 <SEP> 9,13 <SEP> O/a



  Process for the preparation of a hitherto unknown acid amide-like piperidine derivative It has been found that the hitherto unknown 1-methyl-1- (p-ethoxy-benzoyl-amino) piperidine of the following formula can be obtained
EMI0001.0005
  
EMI0001.0006
  
    <SEP> by <SEP> and <SEP> act on <SEP> 1-methyl-l-aniino piperidine <SEP> p-iithoxy-benzoylechloride <SEP>
<tb> lets.
<tb>



  <I> Example </I>
<tb> To <SEP> a <SEP> solution <SEP> of <SEP> 63.0 <SEP> g <SEP> p -, #, tlioxy-ben zoyl chloride <SEP> (1 <SEP> mol <SEP> + <SEP> 10 <SEP> 0 / a <SEP> excess) <SEP> in
<tb> 150 <SEP> em3 <SEP> benzene. <SEP> becomes <SEP> at <SEP> room temperature
<tb> a <SEP> solution <SEP> of <SEP> 35.0 <SEP> g <SEP> 1-methyl-4-amino-pipe ridin <SEP> (l. <SEP> 1o1) <SEP> in <SEP> 150 <SEP> em3 <SEP> Benzene <SEP> added dropwise. It is left to stand overnight and cooked for another hour on the Pücldluss. The benzene solution is mixed with the precipitate with 300 cin3 1.5-n.

   Hydrochloric acid shaken out, the aqueous extract with 3-l1. Sodium hydroxide solution phenolphtalein-alka.liseh ordered and the alis-falling base, the 1-methyl-4- (p-ethoxy-benzoylamiiio) -piperidine, sucked off. and recrystallized from eight times the amount of acetone. 182-181.

    
EMI0001.0020
  
    C15112202N2 <SEP> Ber. <SEP> C <SEP> 68.67 <SEP> 118.45 <SEP> N <SEP> 10.68 <SEP>%
<tb> <B> GU </B> <SEP> ef. <SEP> 68.61 <SEP> 9.08 <SEP> 10.841 / o If the acid amide is used in the equivalent amount 1-n. Dissolved hydrochloric acid, the solution concentrated to dryness in vacuo at 50, the residue in four times the amount of abs. Dissolve alcohol at the boil and add two to three times the amount of ether to the solution,

   so the 1-Hydroelilorid des 1.-Methyl.-1- (p-ethoxy - benzoylamino) - piperidine precipitates in crystalline form. M.p. 213-216.
EMI0001.0035
  
    C15112202N2 <SEP> - <SEP> HC1 <SEP> - <SEP> H20 <SEP> At '. <SEP> C <SEP> 56.86 <SEP> 117.95 <SEP> N <SEP> 8.81 <SEP> 0 / a
<tb> Ctef. <SEP> 56.17 <SEP> 8.07 <SEP> 9.13 <SEP> O / a

Claims (1)

P ATENTANSPRU CII Verfahren zur Flerstellung des bisher un bekannten 1 - Metlivl -1- (p - äthoxy - benzoy l amino)-piperidins, dadurch gekennzeichnet, dass man 1-Methyl-l-amino-piperidin mit p Äthoxy-benzoy lchlarid zur Umsetzung bringt. P ATENTANSPRU CII Process for the production of the previously unknown 1 - Metlivl -1- (p - ethoxy - benzoy l amino) piperidine, characterized in that 1-methyl-l-aminopiperidine with p ethoxy-benzoy lchlarid for the implementation brings. 1-llethy1-1- (p-äthoxy -b enzoy l.amino) -pipe- ridin ist. eine bei Zimmertemperatur feste kri stallisierte Base vom Sinp. 7.82-181 , die ein. Hydrochlorid bildet, das bei 213-216 schmilzt. Das Endprodukt soll therapeutisch verwendet werden. 1-llethy1-1- (p-ethoxy -b enzoy 1.amino) -piperidine is. a solid at room temperature crystallized base from Sinp. 7.82-181, the a. Forms hydrochloride which melts at 213-216. The end product is intended to be used therapeutically.
CH316618D 1953-01-20 1953-01-20 Process for the preparation of a previously unknown acid amide-like piperidine derivative CH316618A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH316618T 1953-01-20
CH740307X 1953-01-20

Publications (1)

Publication Number Publication Date
CH316618A true CH316618A (en) 1956-10-15

Family

ID=25736085

Family Applications (1)

Application Number Title Priority Date Filing Date
CH316618D CH316618A (en) 1953-01-20 1953-01-20 Process for the preparation of a previously unknown acid amide-like piperidine derivative

Country Status (1)

Country Link
CH (1) CH316618A (en)

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