CH301675A - 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
CH301675A
CH301675A CH301675DA CH301675A CH 301675 A CH301675 A CH 301675A CH 301675D A CH301675D A CH 301675DA CH 301675 A CH301675 A CH 301675A
Authority
CH
Switzerland
Prior art keywords
nicotinic acid
acid amide
preparation
ethyl
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 CH301675A publication Critical patent/CH301675A/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     disubsti-          tuierten        Nicotinsäureamids    der Formel  
EMI0001.0007     
    welches dadurch gekennzeichnet ist, dass man  einen reaktionsfähigen Ester des Alkohols der  Formel  
EMI0001.0008     
         2s    mit einer den Rest  
EMI0001.0010     
    abgebenden Verbindung umsetzt.  



  Als den Rest     II    abgebende Verbindungen  kommen insbesondere das     Pyrrol.idin    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-2'-        pyrrolidino    -     äthyl)    ]     -amid     bildet ein nahezu farbloses Öl, welches unter  0,08 mm bei 245-250  siedet und sich     gut    in  verdünnten Säuren, wenig in Wasser und     Pe-          troläther    löst. Das Chlorhydrat schmilzt aus       Methylisobutylketon    umkristallisiert bei 188  bis 190 .

   Die neue Verbindung soll als     Spas-          molytikum    und als     Zwischenprodukt    zur Her  stellung weiterer Derivate     Verwendung    fin  den.  



  <I>Beispiel:</I>  36,5g     N-(,B-Chlor-äthyl)-N-(1,2-diphenyl-          äthyl)-nicotinsäureamid    werden mit 8,0 g       Pyrrolidin    und 100     em3    Benzol im Autokla  ven 5 Stunden bei 100  geschüttelt.

       Ansehlie-          fiend    dampft man zur Trockne ein, verrührt  mit     2n-Natronlauge    und nimmt das sich ab  scheidende Öl in Chloroform auf, trocknet,  verdampft und destilliert den Rückstand im       1EIochvakuum.         Man erhält so das unter 0,08 mm bei 245  bis 250  siedende     Nicotinsäure-[N-(1,2-diphe-          nyl-äthyl)-N-(2'-pyrrolidino-äthyl)        ]-amid    in  sehr guter Ausbeute als fast farbloses Öl. Das  Chlorhydrat der Base     schmilzt    aus     Methyliso-          butyllzeton    umkristallisiert bei 188-190 .



  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
         2s with one the rest
EMI0001.0010
    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 react. to be brought.



  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-2'-pyrrolidino-ethyl)] -amide obtained in this way forms an almost colorless oil which boils below 0.08 mm at 245-250 and dissolves well in dilute acids, little in water and petroleum ether. The chlorohydrate melts from methyl isobutyl ketone recrystallized at 188-190.

   The new compound is intended to be used as a spasmodic and as an intermediate product for the manufacture of other derivatives.



  <I> Example: </I> 36.5 g of N - (, B-chloro-ethyl) -N- (1,2-diphenyl-ethyl) -nicotinic acid amide are placed in an autoclave with 8.0 g of pyrrolidine and 100 em3 of benzene Shaken at 100 for 5 hours.

       Subsequently, it is evaporated to dryness, stirred with 2N sodium hydroxide solution and the oil which separates out is taken up in chloroform, dried, evaporated and the residue is distilled in a 1EIochvakuum. The nicotinic acid [N- (1,2-diphenyl-ethyl) -N- (2'-pyrrolidino-ethyl)] -amide boiling below 0.08 mm at 245 to 250 is obtained in a very good yield as almost colorless oil. The chlorohydrate of the base melts from methyl isobutyltone recrystallized at 188-190.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen di- substituierten Nicotinsäureamids der Formel EMI0002.0010 dadurch gekennzeichnet, dass man einen reak tionsfähigen Ester des Alkohols der Formel EMI0002.0013 mit einer den Rest EMI0002.0014 und als Zwischenprodukt Verwendung finden. abgebenden Verbindung umsetzt. PATENT CLAIM: Process for the production of a new di-substituted nicotinic acid amide of the formula EMI0002.0010 characterized in that there is a reactive ester of the alcohol of the formula EMI0002.0013 with one the rest EMI0002.0014 and used as an intermediate product. transferring connection. Das so erhaltene Nicotinsäure -[N-(1,2-di- phenyl-äthyl )-N- (2'-pyr rolidino-äthyl) ] - amid bildet. ein nahezu farbloses Öl, welches unter 0,08 mm bei 245 bis 250 siedet und sieh leicht. in verdünnten Säuren, wenig in Wasser und Petroläther löst. Das Chlorhydrat schmilzt aus Methvjiso- butylketon umkristallisiert bei 188-190 . Die Verbindung soll als Spasmolytikum The nicotinic acid thus obtained - [N- (1,2-diphenyl-ethyl) -N- (2'-pyrrolidino-ethyl)] - forms amide. an almost colorless oil which boils below 0.08 mm at 245 to 250 and looks easy. Dissolves in dilute acids, little in water and petroleum ether. The chlorohydrate melts from Methvjisobutylketon recrystallized at 188-190. The compound is said to be used as an antispasmodic
CH301675D 1951-03-01 1951-04-03 Process for the preparation of a new disubstituted nicotinic acid amide. CH301675A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH294511T 1951-03-01
CH301675T 1951-04-03

Publications (1)

Publication Number Publication Date
CH301675A true CH301675A (en) 1954-09-15

Family

ID=25733491

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301675D CH301675A (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) CH301675A (en)

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