CH297714A - 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
CH297714A
CH297714A CH297714DA CH297714A CH 297714 A CH297714 A CH 297714A CH 297714D A CH297714D A CH 297714DA CH 297714 A CH297714 A CH 297714A
Authority
CH
Switzerland
Prior art keywords
nicotinic acid
preparation
acid amide
new
compound
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 CH297714A publication Critical patent/CH297714A/en

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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)
  • Pyridine Compounds (AREA)

Description

  

      Verfahren    zur Herstellung eines neuen     disubstituierten        Nicotinsäureamids.            (@eenatand    der     Erfindung    ist ein Ver  fahren zur     Herstellung    eines netten     disubsti-          tuierten        Nicotinsäureamids    der Formel  
EMI0001.0010     
         welches    dadurch gekennzeichnet ist, dass man  die Verbindung der Formel  
EMI0001.0012     
         deea        rboxyl    legt.  



       1)ie        Decarboxylierung    kann     dureh    Er  hitzen: in An- oder Abwesenheit eines     Lö-          sun        Is-    bzw.     Verdünnungsmittels    erfolgen..  



  Die Verbindung der Formel I kann bei  spielsweise durch     rmsetzung    von     Chinolin-          @äureanht-drid    mit     N-(1,2=D.iphenjl-äthyl)-N-          (''-niorph(Ylino-äthyl)-amiti        o-ewonnen    werden..

    Es ist, auch möglich, die gebildete Verbin  dung der     Formel    I ohne     Isolierung,    zu     deear-          hoxviieren.       Das so erhaltene     Nicotinsäure-N-(1,2-di-          phenyl    -     äthy    1)     -_N-        (2-morpholino    -     äthyl)    -     amid     bildet ein nahezu farbloses Öl,     welches        unter     0,08 mm bei     280-290     siedet     Lund    sich gut.

    in verdünnten Säuren, wenig in Wasser und       Petroläther    löst-. Das     Chloroplatinat    der Ver  bindung schmilz bei 185-188 unter Zer  setzung.  



  Die neue Verbindung soll     als        Spasmolyti-          kum    und als     Zwischenprodukt    zur     Herstel-          hing    weiterer Derivate Verwendung finden.

         Beispiel:     Zu 75 g geschmolzenem     Chinolinsäureanhy-          drid        werden;    innert 10 Minuten 77,5g     N-(1,2-          Diphenyl-äthyl)    -N-     (2-morpholino-äthyl)        -amin          zugetropft,

      wobei die Temperatur -um     etwa    30        steigt.        Anschliessend    erhitzt man 15 Minuten  auf 160  und lässt darnach     die        Schmelze        er-          kalten.        Die        glasig        erstarrte        Masse        wird        in     gelöst, mit Natronlauge versetzt  und mit Chloroform     extrahiert.    Das Chloro  form wird nach dem     Trocknen    über  Natriumsulfat verdampft.

   Darauf löst man  den Rückstand - einen schwarzen, dicken  Sirup - in Äther, behandelt mit Kohle  und filtriert. Das Filtrat wird mit     2n-          Salzsäure    ausgezogen und der salzsaure Aus  zug ebenfalls mit Kohle behandelt, filtriert,  wieder alkalisch gemacht und erschöpfend       ausgeäthert.    Nach dem Verdampfen des  Äthers und Destillieren des Rückstandes im       Hoehvakuum    gewinnt man das     unter    0,08 min  bei     280-290     siedende Nicot-insäure-N-(1,2-           diphenyl-äthyl)-M(2-morpholino-äthyl)-amid     in befriedigender Ausbeute.  



  Die neue Verbindung löst sich leicht in       verdünnten    Säuren, weniger gut in Wasser  und     Petroläther.    Das     Chloroplat.inat    der Ver  bindung schmilzt bei 185-188  unter     Zer-          setzung.  



      Process for the preparation of a new disubstituted nicotinic acid amide. (@eenatand of the invention is a process for the production of a nice disubstituted nicotinic acid amide of the formula
EMI0001.0010
         which is characterized in that the compound of the formula
EMI0001.0012
         deea rboxyl lays.



       1) The decarboxylation can be carried out by heating: in the presence or absence of a solvent or diluent.



  The compound of the formula I can be obtained, for example, by reacting quinoline acid anhydride with N- (1,2 = D.iphenyl-ethyl) -N- ('' -niorph (ylino-ethyl) -amite) ..

    It is also possible to deearhoxvate the compound of the formula I formed without isolation. The nicotinic acid-N- (1,2-diphenyl-ethy 1) -N- (2-morpholino-ethyl) -amide thus obtained forms an almost colorless oil, which boils below 0.08 mm at 280-290 Well.

    Dissolves in dilute acids, little in water and petroleum ether. The chloroplatinate of the compound melts at 185-188 with decomposition.



  The new compound is said to be used as an antispasmodic and as an intermediate for the production of other derivatives.

         Example: Add to 75 g of molten quinolinic anhydride; 77.5g of N- (1,2-diphenylethyl) -N- (2-morpholino-ethyl) amine were added dropwise within 10 minutes,

      the temperature rising by about 30. The mixture is then heated to 160 for 15 minutes and then allowed to cool the melt. The glassy solidified mass is dissolved in, mixed with sodium hydroxide solution and extracted with chloroform. The chloro form is evaporated after drying over sodium sulfate.

   The residue - a thick black syrup - is then dissolved in ether, treated with charcoal and filtered. The filtrate is extracted with 2N hydrochloric acid and the hydrochloric acid extract is also treated with charcoal, filtered, made alkaline again and exhaustively extracted with ether. After evaporation of the ether and distillation of the residue in a high vacuum, nicotinic acid-N- (1,2-diphenyl-ethyl) -M (2-morpholino-ethyl) -amide is obtained, which boils at 280-290 for under 0.08 min in a satisfactory yield.



  The new compound dissolves easily in dilute acids, less readily in water and petroleum ether. The chloroplatinate of the compound melts at 185-188 with decomposition.

Claims (1)

PATENTANSP<B>RU</B>CH Verfahren zur Herstellung eines neuen disubstituiertenNicotinsäureamids der Formel EMI0002.0009 dadurch gekennzeichnet, dass man die Ver bindung der Formel EMI0002.0011 decarboxyliert. Das so erhaltene Nicotinsäaire-N-(1"2,-di- phenyl - äthyl) -N- ('2-morpholino - äthy 1) - amid bildet ein nahezu farbloses Öl, welches unter 0,08 mm bei 2, PATENTANSP <B> RU </B> CH Process for the preparation of a new disubstituted nicotinic acid amide of the formula EMI0002.0009 characterized in that one has the compound of the formula EMI0002.0011 decarboxylated. The nicotinic acid-N- (1 "2, -diphenyl-ethyl) -N- ('2-morpholino-ethy 1) - amide obtained in this way forms an almost colorless oil, which is less than 0.08 mm at 2, 80-290 siedet und sich leicht in verdünnten Säuren und wenig in Wasser und Petroläther löst. Das Chloroplatinat schmilzt bei 185-188" unter Zersetzung. Die neue Verbindung soll als :Spasmolyti- kum und als Zwischenprodukt Verwendung finden- 80-290 boils and dissolves easily in dilute acids and a little in water and petroleum ether. The chloroplatinate melts at 185-188 "with decomposition. The new compound is said to be used as an antispasmodic and as an intermediate product.
CH297714D 1951-03-01 1951-03-01 Process for the preparation of a new disubstituted nicotinic acid amide. CH297714A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH297714T 1951-03-01
CH297720T 1951-03-01
CH293815T 1951-03-01

Publications (1)

Publication Number Publication Date
CH297714A true CH297714A (en) 1954-03-31

Family

ID=27178191

Family Applications (1)

Application Number Title Priority Date Filing Date
CH297714D CH297714A (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) CH297714A (en)

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