CH299262A - Process for the preparation of a new disubstituted nicotinic acid amide. - Google Patents

Process for the preparation of a new disubstituted nicotinic acid amide.

Info

Publication number
CH299262A
CH299262A CH299262DA CH299262A CH 299262 A CH299262 A CH 299262A CH 299262D A CH299262D A CH 299262DA CH 299262 A CH299262 A CH 299262A
Authority
CH
Switzerland
Prior art keywords
nicotinic acid
ethyl
acid amide
preparation
new
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag 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 Cilag Ag filed Critical Cilag Ag
Publication of CH299262A publication Critical patent/CH299262A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

Landscapes

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

Description

  

      Verfahren        zur    Herstellung eines neuen     disubstituierten        Nicotinsäureamids.       Gegenstand der Erfindung     ist    ein Verfah  ren zur     Herstellung    eines neuen     disubstituier-          ten        Nicotinsäureamids    der Formel  
EMI0001.0010     
    welches dadurch gekennzeichnet ist, dass man  eine das     Nicotinyl-Radikal    liefernde Verbin  dung mit einer den Rest  
EMI0001.0012     
    liefernden Verbindung umsetzt.  



  Als den     Nicotinsäurerest    liefernde Verbin  dung seien beispielsweise erwähnt:  Die     Nicotinsäure    selbst, ihre Ester, ihre       Halogenide,    ihr     Azid    und ihr     Anhydrid    bzw.  ihre gemischten     Anhydride,    z. B. mit Phos  phorsäure, Schwefelsäure     usf.    Als den Amin  rest liefernde     Verbindiuigen    seien zum Bei  spiel das     N-(1,2-Diphenyl-äthyl)-N-(2'-piperi-          dino-äthyl)-amin    selbst sowie seine     N-Metall-          derivate    erwähnt.

   Die     Umsetzung    kann in An-    oder Abwesenheit eines     Lösungs-    bzw. Ver  dünnungsmittels und eines basischen Konden  sationsmittels erfolgen. Als Kondensationsmit  tel kann auch das genannte Amin selbst die  nen.  



  Das so erhaltene     Nicotinsäure-[N-(1,2-di-          phenyl-ätb.yl)-N-        (2'-piperidino    -     äthyl)    ] -     amid     bildet ein gelbliches Öl, welches     unter    0,08 mm  bei 250-260  siedet und sich gut     in    verdünn  ten Säuren,     \wenig    in Wasser und     Petroläther     löst.  



  Die Verbindung besitzt wertvolle     spasmo-          lytische    Eigenschaften und soll deshalb als  Arzneimittel, aber auch als Zwischenprodukt  zur Herstellung weiterer Derivate Verwen  dung finden.  



  <I>Beispiel 1:</I>  30 g     N-(1,2-Diphenyl-äthyl)-N-(2'-piperi-          dino-äthyl)-amin        und    35 g     Nicotinsäureanhy-          drid    werden in je 250     ems    warmem     Benzol     gelöst, miteinander vermischt und mit 21 g  geglühter Pottasche 5     Stunden    gekocht.

   Nach  dem Erkalten wird einige Male mit verdünn  ter Natronlauge durchgeschüttelt, die Benzol  schicht dann mit Salzsäure ausgezogen, die       Salzsäurelösung    filtriert, mit Natronlauge al  kalisch gemacht und das obenauf schwim  mende Öl in Chloroform aufgenommen: Nach  dem Verdampfen des Chloroforms wird der  Rückstand im Hochvakuum destilliert. Man  erhält so 32g     Nicotüisäure-[N-(1,2-diphenyl-          äthyl)-N-(2'-piperidino-äthyl)]-amid    als gelb  liches Öl, das unter 0,08 mm bei 250-260  sie  det, Die neue Verbindung löst sich leicht in      verdünnten Säuren, weniger gut in Wasser  und     Petroläther.     



  <I>Beispiel 2:</I>  Die gleiche Verbindung erhält man in  guter Reinheit und Ausbeute, wenn man     Nico-          tinsäure    und     N-(1,2-Diphenyl-äthyl)-N-(2'-pi-          peridino-äthyl)-amin    bei erhöhter Temperatur  zusammen erhitzt und das Reaktionsgemisch  analog wie in Beispiel 1 beschrieben     aufarbei-          tpt_  



      Process for the preparation of a new disubstituted nicotinic acid amide. The invention relates to a process for the preparation of a new disubstituted nicotinic acid amide of the formula
EMI0001.0010
    which is characterized in that one of the nicotinyl radical supplying connection with a remainder
EMI0001.0012
    the supplying connection.



  As the connection supplying nicotinic acid, for example: nicotinic acid itself, its esters, its halides, its azide and its anhydride or its mixed anhydrides, e.g. B. with phosphoric acid, sulfuric acid, etc. The amine residue supplying compounds are, for example, N- (1,2-diphenylethyl) -N- (2'-piperidinoethyl) amine itself and its N -Metal- derivatives mentioned.

   The reaction can take place in the presence or absence of a solvent or diluent and a basic condensation agent. The amine itself can also be used as the condensation agent.



  The nicotinic acid [N- (1,2-diphenyl-ätb.yl) -N- (2'-piperidino-ethyl)] amide thus obtained forms a yellowish oil, which is below 0.08 mm at 250-260 boils and dissolves well in dilute acids, \ little in water and petroleum ether.



  The compound has valuable spasmolytic properties and should therefore be used as a medicament, but also as an intermediate for the production of further derivatives.



  <I> Example 1: </I> 30 g of N- (1,2-diphenyl-ethyl) -N- (2'-piperidino-ethyl) -amine and 35 g of nicotinic anhydride are heated to 250 ems each Benzene dissolved, mixed together and boiled with 21 g of calcined potash for 5 hours.

   After cooling, it is shaken a few times with dilute sodium hydroxide solution, the benzene layer is then extracted with hydrochloric acid, the hydrochloric acid solution filtered, made alkaline with sodium hydroxide solution and the oil floating on top taken up in chloroform: After the chloroform has evaporated, the residue is distilled in a high vacuum . This gives 32g of nicotiic acid [N- (1,2-diphenyl-ethyl) -N- (2'-piperidino-ethyl)] amide as a yellowish oil which under 0.08 mm at 250-260 it det, The new compound dissolves easily in dilute acids, less readily in water and petroleum ether.



  <I> Example 2: </I> The same compound is obtained in good purity and yield if nicotinic acid and N- (1,2-diphenyl-ethyl) -N- (2'-piperidino-ethyl) are used ) -amine is heated together at an elevated temperature and the reaction mixture is worked up analogously as described in Example 1.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen di- substituierten Nicotinsäureamids der Formel EMI0002.0011 dadurch gekennzeichnet, dass man eine das Nicotinyl-Radikal liefernde Verbindung mit einer den Rest EMI0002.0015 liefernden Verbindung umsetzt. PATENT CLAIM Process for the production of a new di-substituted nicotinic acid amide of the formula EMI0002.0011 characterized in that one provides the nicotinyl radical with a the remainder EMI0002.0015 the supplying connection. Das so erhaltene Nicotinsäure-[N-(1,2-di- phenyl-äthyl)-N-(2'-piperidino-äthyl) ] -amid bildet ein leicht gelblich gefärbtes Öl, welches unter 0,08 mm bei 250-260 siedet und sich leicht in verdünnten Säuren und wenig in Wasser und Petroläther löst. Die Verbindung soll als Spasmolytikum und als Zwischenprodukt Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als das Nicotinyl- Radikal liefernde Verbindung Nicotinsäure- anhydrid verwendet. The nicotinic acid [N- (1,2-diphenyl-ethyl) -N- (2'-piperidino-ethyl)] -amide obtained in this way forms a slightly yellowish oil, which is below 0.08 mm at 250-260 boils and dissolves easily in dilute acids and a little in water and petroleum ether. The compound is said to be used as an antispasmodic and as an intermediate product. SUBCLAIM: Process according to patent claim, characterized in that nicotinic anhydride is used as the compound providing the nicotinyl radical.
CH299262D 1951-03-01 1951-03-01 Process for the preparation of a new disubstituted nicotinic acid amide. CH299262A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH299269T 1951-03-01
CH299262T 1951-03-01
CH296180T 1951-03-01

Publications (1)

Publication Number Publication Date
CH299262A true CH299262A (en) 1954-05-31

Family

ID=27178225

Family Applications (1)

Application Number Title Priority Date Filing Date
CH299262D CH299262A (en) 1951-03-01 1951-03-01 Process for the preparation of a new disubstituted nicotinic acid amide.

Country Status (1)

Country Link
CH (1) CH299262A (en)

Similar Documents

Publication Publication Date Title
CH299262A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299266A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299260A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299261A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299267A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299264A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299263A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299265A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299259A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299257A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH299258A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
DE1097995B (en) Process for the preparation of phenthiazine derivatives
DE1038047B (en) Process for the preparation of N-aminoalkylated iminodibenzyls and their salts
CH296180A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
AT214441B (en) Process for the production of new benzothiazoles and their salts
AT289809B (en) Process for the production of new morphanthridines and of their acid addition salts
CH269082A (en) Process for the preparation of a diaryl-butenyl-amine.
CH301673A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH301675A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH297713A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH305347A (en) Process for the preparation of a therapeutically valuable compound of the quinoline series.
CH301676A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH301678A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH301674A (en) Process for the preparation of a new disubstituted nicotinic acid amide.
CH300469A (en) Process for the preparation of an imidazole derivative.