CH301678A - 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
CH301678A
CH301678A CH301678DA CH301678A CH 301678 A CH301678 A CH 301678A CH 301678D A CH301678D A CH 301678DA CH 301678 A CH301678 A CH 301678A
Authority
CH
Switzerland
Prior art keywords
nicotinic acid
preparation
acid amide
new disubstituted
formula
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 CH301678A publication Critical patent/CH301678A/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

Description

  

  Verfahren     zur    Herstellung eines neuen     disubstituierten        Nicotinsäureamids.       Gegenstand der Erfindung ist ein Verfah  ren zur Herstellung eines neuen     disubstituier-          ten        Nicotinsäureamids    der Formel  
EMI0001.0007     
    welches dadurch gekennzeichnet ist, dass man  einen reaktionsfähigen Ester des Alkohols der  Formel  
EMI0001.0008     
    mit einer den Rest  
EMI0001.0009     
    abgebenden Verbindung umsetzt.  



  Als den Rest     II    abgebende Verbindungen  kommen insbesondere das     Pyrrolidin    selbst  und seine     N-Metallderivate    in Betracht.    Als reaktionsfähige Ester des     Alkohols    I  kann man beispielsweise einen Halogenwasser  stoffsäure-, einen Schwefelsäure-, einen     Alkyl-          bzw.        Arylsulfonsäureester    verwenden. Statt  des freien     Aminoalkoholesters    (I) und des  freien Amins     (II)    können auch ihre Salze zur  Reaktion gebracht werden.  



  Die Umsetzung kann in An- oder Abwesen  heit eines     Lösungs-    bzw. Verdünnungsmittels  und eines Kondensationsmittels durchgeführt  werden.  



  Das so erhaltene     Nicotinsäure-[N-(1,2-di-          phenyl-äthyl)        -N-(3'-pyrrolidino-propyl)    ]     -amid     bildet ein nahezu farbloses Öl, welches unter  0,08 mm bei 250-255  siedet und sich gut in  verdünnten Säuren, wenig in Wasser und     Pe-          troläther    löst. Das Chlorhydrat schmilzt aus       -'VIethylisobutylketon    umkristallisiert bei     12"i     bis 130 . Die neue Verbindung soll als     Spas-          molytikum    und als     Zwischenprodukt    zur Her  stellung weiterer Derivate Verwendung fin  den.  



  <I>Beispiel:</I>  37,9g     N-(y-Chlor-propyl)-N-(1,2-diphenyl-          äthyl)-nicotinsäureamid    werden mit 8,0 g     Pyr-          rolidin    und 150     em3    Benzol im     Autoklaven     Stunden bei     -100     geschüttelt. Anschliessend  dampft man zur Trockne ein, verrührt mit       2n-Natronlauge    und nimmt das sich abschei  dende Öl in Chloroform auf, trocknet, ver  dampft und destilliert den Rückstand im  Hochvakuum.

        Man erhält so das unter 0,08 mm bei 250  bis 255  siedende     Nicotinsäure-[N-(1,2-diphe-          nyl-äthyl)-N-(3'-pyrrolidino-propyl)    ]     -amid    in  guter Ausbeute als fast farbloses Öl. Das Chlor  hydrat der Base schmilzt aus     Methylisobutyl-          keton    umkristallisiert bei 127-130 .



  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
EMI0001.0007
    which is characterized in that one has a reactive ester of the alcohol of the formula
EMI0001.0008
    with one the rest
EMI0001.0009
    transferring connection.



  Particularly suitable compounds which donate the radical II are pyrrolidine itself and its N-metal derivatives. The reactive ester of alcohol I can be, for example, a hydrogen halide, a sulfuric acid, an alkyl or aryl sulfonic acid ester. Instead of the free amino alcohol ester (I) and the free amine (II), their salts can also be reacted.



  The reaction can be carried out in the presence or absence of a solvent or diluent and a condensing agent.



  The nicotinic acid- [N- (1,2-diphenyl-ethyl) -N- (3'-pyrrolidino-propyl)] -amide obtained in this way forms an almost colorless oil which boils below 0.08 mm at 250-255 and dissolves well in dilute acids, little in water and petroleum ether. The chlorohydrate melts from -'VIethylisobutylketon recrystallized at 12 "i to 130. The new compound is to be used as a spasmolytic and as an intermediate for the production of further derivatives.



  <I> Example: </I> 37.9 g of N- (γ-chloro-propyl) -N- (1,2-diphenyl-ethyl) -nicotinic acid amide are mixed with 8.0 g of pyrrolidine and 150 cubic meters of benzene in the autoclave Shaken at -100 hours. It is then evaporated to dryness, stirred with 2N sodium hydroxide solution and the separating oil is taken up in chloroform, dried, evaporated and the residue is distilled in a high vacuum.

        Nicotinic acid [N- (1,2-diphenyl-ethyl) -N- (3'-pyrrolidino-propyl)] -amide, boiling below 0.08 mm at 250 to 255, is obtained in good yield as an almost colorless one Oil. The chlorine hydrate of the base melts from methyl isobutyl ketone recrystallized at 127-130.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen di- substituierten Nieotinsäureamids der Formel EMI0002.0009 dadurch gekennzeichnet, dass man einen reak tionsfähigen Ester des Alkohols der Formel EMI0002.0010 abgebenden Verbindung umsetzt. Das so erhaltene Nicotinsäure-[N-(1,2-di- pheny 1-äthyl) -N-(3'-pyrrolidino-p ropyl) ] -amid bildet ein nahezu farbloses Öl, welches unter 0,08 mm bei 250-255 siedet und sich leicht in verdünnten Säuren, PATENT CLAIM: Process for the preparation of a new disubstituted Nieotinsäureamids of the formula EMI0002.0009 characterized in that there is a reactive ester of the alcohol of the formula EMI0002.0010 transferring connection. The nicotinic acid [N- (1,2-dipheny 1-ethyl) -N- (3'-pyrrolidino-propyl)] -amide obtained in this way forms an almost colorless oil, which is less than 0.08 mm at 250- 255 boils and easily dissolves in dilute acids, wenig in Wasser und Petroläther löst. Das Chlorhydrat schmilzt aus Methylisobu- tylketon umkristallisiert bei 127-130 . Die Verbindung soll als Spasmolytikum und als Zwischenprodukt Verwendung finden. dissolves little in water and petroleum ether. The chlorohydrate melts from methyl isobutyl ketone recrystallized at 127-130. The compound is said to be used as an antispasmodic and as an intermediate product.
CH301678D 1951-03-01 1951-04-03 Process for the preparation of a new disubstituted nicotinic acid amide. CH301678A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH294511T 1951-03-01
CH301678T 1951-04-03

Publications (1)

Publication Number Publication Date
CH301678A true CH301678A (en) 1954-09-15

Family

ID=25733494

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301678D CH301678A (en) 1951-03-01 1951-04-03 Process for the preparation of a new disubstituted nicotinic acid amide.

Country Status (1)

Country Link
CH (1) CH301678A (en)

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