CH316620A - 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
CH316620A
CH316620A CH316620DA CH316620A CH 316620 A CH316620 A CH 316620A CH 316620D A CH316620D A CH 316620DA CH 316620 A CH316620 A CH 316620A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
previously unknown
methyl
acid amide
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 CH316620A publication Critical patent/CH316620A/en

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  • Hydrogenated Pyridines (AREA)

Description

  

  <B>Verfahren zur Herstellung eines bisher unbekannten</B>     säureamidartigen        Piperidinderivates       Es wurde gefunden, dass man zum bisher unbekannten     1-Methyl-4-(p-metIiyl-benzoyl-          amino)-piperidin    der folgenden Formel  
EMI0001.0005     
         gelangt,    indem man auf     1-Methyl-4-a.mino-          piperidin        p--Nletliyl-benzoylehlorid    einwirken  lässt.  



       Beispiel     Zu einer Lösung von 53,0 g     p-Methyl-ben-          zoylehloricl    (1     11o1        -i-    -10     o/a        Überschuss)    in  150     em3    Benzol wird bei     Zimmertemperatur     eine Lösung von 35,0 g     1-Methy        1-4-amino-          piperidin    (1     Mol)

      in 150     em3    Benzol     zuge-          tropft.        und    über Nacht     stehengelasseti.    Am    andern Tag wird noch 1 Stunde am Rück  fluss gekocht. Die     Benzollösung    wird mit dem  Niederschlag mit 300     cm3    1,5-n.     Salzsäure    aus  geschüttelt, der wässerige     AiLszug    mit 3-n.

    Natronlauge     phenolphtalein-alkaliseh    gestellt  und die ausgefallene Base, das     1-Methyl-4-          p    -     methy    1-     benzoylamino)    -     piperidin,        abge-          nutseht    und aus der fünfzehnfachen Menge  30      /aigem        wässerigem    Alkohol umkristalli  siert.     Smp.    189-191 .

    
EMI0001.0043     
  
    C14H2OON2 <SEP> Ber. <SEP> C <SEP> 72,36 <SEP> H <SEP> 8,68 <SEP> N <SEP> 12,06 <SEP> O/o
<tb>  Gef. <SEP> 72,65 <SEP> 9,43 <SEP> 12,469/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 Lösung mit der    vierfachen Menge Äther versetzt, so fällt das       Hydrochlorid    des     1-Methyl-4-(p-methyl-ben-          zoylamino)-piperidins    kristallin aus.     Smp.    239  bis 242   
EMI0001.0050     
  
    C1,1112oONT2 <SEP> # <SEP> HC' <SEP> Ber.

   <SEP> C <SEP> 62,54 <SEP> H <SEP> 7,88 <SEP> N <SEP> 10,42 <SEP>  /o
<tb>  Gef. <SEP> 62,97 <SEP> 7,66 <SEP> <B>10,88%</B>



  <B> Process for the preparation of a previously unknown </B> acid amide-like piperidine derivative It has been found that the previously unknown 1-methyl-4- (p-methylbenzoylamino) piperidine of the following formula can be obtained
EMI0001.0005
         obtained by letting p-Nletliyl-benzoylehlorid act on 1-methyl-4-a.mino-piperidine.



       EXAMPLE To a solution of 53.0 g of p-methylbenzoylehloricl (1 11o1 -i- -10 o / a excess) in 150 cubic meters of benzene, a solution of 35.0 g of 1-methyl 1-4- is added at room temperature. aminopiperidine (1 mol)

      in 150 cubic meters of benzene was added dropwise. and left to stand overnight. The next day they cook for another hour on the reflux. The benzene solution is with the precipitate with 300 cm3 1.5-n. Hydrochloric acid shaken off, the aqueous draw with 3-n.

    Sodium hydroxide solution made phenolphtalein-alkaliseh and the precipitated base, the 1-methyl-4-p-methy 1-benzoylamino) piperidine, removed and recrystallized from fifteen times the amount of 30% aqueous alcohol. 189-191.

    
EMI0001.0043
  
    C14H2OON2 <SEP> Ber. <SEP> C <SEP> 72.36 <SEP> H <SEP> 8.68 <SEP> N <SEP> 12.06 <SEP> O / o
<tb> Gef. <SEP> 72.65 <SEP> 9.43 <SEP> 12.469 / 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. Alcohol is dissolved at the boil and the solution is mixed with four times the amount of ether, the 1-methyl-4- (p-methyl-benzoylamino) piperidine hydrochloride precipitates in crystalline form. M.p. 239 to 242
EMI0001.0050
  
    C1,1112oONT2 <SEP> # <SEP> HC '<SEP> Ber.

   <SEP> C <SEP> 62.54 <SEP> H <SEP> 7.88 <SEP> N <SEP> 10.42 <SEP> / o
<tb> Found <SEP> 62.97 <SEP> 7.66 <SEP> <B> 10.88% </B>

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung des bisher un bekannten 1-llethyl-4-(p-met.hyl-benzoyl- amino)-piperidins, dadurch gekennzeichnet, dass man 1-Methy 1-4-amino-piperidin mit p Methyl-benzoylchlorid zur Umsetzung bringt. 1-Methy 1-4- (p-methyl-benzoylamino)-pipe- ridin ist eine bei Zimmertemperatur feste kristallisierte Base vom Smp. 189-191 , die ein Hydrochlorid bildet, das bei 239-242 schmilzt. Das Endprodukt soll therapeutisch verwendet werden. PATENT CLAIM Process for the preparation of the previously unknown 1-llethyl-4- (p-meth.hyl-benzoyl-amino) -piperidine, characterized in that 1-methyl 1-4-aminopiperidine is reacted with p-methyl-benzoyl chloride brings. 1-Methy 1-4- (p-methyl-benzoylamino) -piperidine is a solid crystallized base at room temperature with a melting point of 189-191 which forms a hydrochloride which melts at 239-242. The end product is intended to be used therapeutically.
CH316620D 1953-01-20 1953-01-20 Process for the preparation of a previously unknown acid amide-like piperidine derivative CH316620A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH316620T 1953-01-20
CH740307X 1953-01-20

Publications (1)

Publication Number Publication Date
CH316620A true CH316620A (en) 1956-10-15

Family

ID=25736087

Family Applications (1)

Application Number Title Priority Date Filing Date
CH316620D CH316620A (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) CH316620A (en)

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