CH311582A - Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents

Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide).

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Publication number
CH311582A
CH311582A CH311582DA CH311582A CH 311582 A CH311582 A CH 311582A CH 311582D A CH311582D A CH 311582DA CH 311582 A CH311582 A CH 311582A
Authority
CH
Switzerland
Prior art keywords
anilide
methyl
preparation
chloro
fatty acid
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 CH311582A publication Critical patent/CH311582A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  



  Verfahren zur Herstellung eines basisch substituierten   Fettsäure-     (2-halogen-6-methyl-anilids).



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6methyl-anilids), welches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1     
   mit Dimet. hylamin umsetzt.    Die Umsetzung kann in An-oder Abwesenheit von   Lösungs-      hzw.    Verdünnungsmitteln und   Anlagerungs-    katalysatoren erfolgen. Vorzugsweise wird wegen der   Leichtflüchtigkeit    des Dimethylamins unter Druck gearbeitet. Als Anlage   rungskatalysatoren benützt man vorteilhaft    quaternäre Ammoniumbasen, wie z. B. Trime  thylbenzylammoniumhydroxyd.   



   Das so erhaltene 8-Dimethylamino-propion  säure- (2-chlor-6-methyl-anilid)    bildet ein fa. rbloses Öl ; dessen Hydrochlorid schmilzt bei 77,   5-79,      5 .    Das neue Anilid soll als Lokal  anästhetikum.    und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.



   Beispiel:
Ein Gemisch von 20 Gewichtsteilen   Acryl-    säure-(2-chlor-6-methyl-anilid), 15   Gewiehts-    teilen Dimethylamin und einigen Tropfen   Trimethylbenzylammoniumhydroxyd    wird im Autoklaven während 20 Stunden auf   145     er  hitzt.    Nach dem Erkalten wird durch die Reaktionsmischung Wasserdampf zwecks Entfernung flüchtiger Anteile geleitet.   Anschlie-    ssend wird verdampft und der Rückstand mit   Petroläther ausgezogen. Man erhält    so das ss Dimetjhylamino-propionsäure-(2-chlor-6-methyl-anilid) als farbloses Öl.  



   PATENTANSPRUCH :
Verfahren zur Herstellung eines basisch substituierten   Fettsäure-(2-ha. logen-6-methyl-      anilids),    dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2     
 mit Dimethylamin umsetzt. Das so erhaltene ss-Dimethylamino-propionsäure-(2-chlor-6-me  thyl-anilid)    ist ein farbloses Öl ; dessen Hydrochlorid schmilzt bei 77,   5-79,    5 . Es soll als   Lokalanästhetikum und    als Zwischenprodukt Verwendung finden. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide).



   The subject of the present patent is a process for the preparation of a new basic substituted fatty acid (2-halo-6methyl-anilide), which is characterized in that a compound of the formula
EMI1.1
   with dimet. hylamine converts. The reaction can be carried out in the presence or absence of solution. Diluents and addition catalysts take place. It is preferable to work under pressure because of the volatility of dimethylamine. As plant approximately catalysts are used advantageously quaternary ammonium bases, such as. B. Trimethylbenzylammonium hydroxide.



   The 8-dimethylamino-propionic acid (2-chloro-6-methyl-anilide) obtained in this way forms a fa. colorless oil; its hydrochloride melts at 77, 5-79, 5. The new anilide is said to be used as a local anesthetic. and as an intermediate for the production of other derivatives.



   Example:
A mixture of 20 parts by weight of acrylic acid (2-chloro-6-methyl-anilide), 15 parts by weight of dimethylamine and a few drops of trimethylbenzylammonium hydroxide is heated to 145 in the autoclave for 20 hours. After cooling, water vapor is passed through the reaction mixture to remove volatile components. It is then evaporated and the residue extracted with petroleum ether. This gives the ss dimethylamino-propionic acid (2-chloro-6-methyl-anilide) as a colorless oil.



   PATENT CLAIM:
Process for the preparation of a basic substituted fatty acid (2-ha. Logen-6-methyl-anilide), characterized in that a compound of the formula
EMI1.2
 reacts with dimethylamine. The ss-dimethylamino-propionic acid (2-chloro-6-methyl-anilide) obtained in this way is a colorless oil; its hydrochloride melts at 77, 5-79, 5. It should be used as a local anesthetic and as an intermediate product.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung eines basisch substituierten Fettsäure- (2-halogen-6-methyl-anilids). Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6methyl-anilids), welches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel EMI1.1 mit Dimet. hylamin umsetzt. Die Umsetzung kann in An-oder Abwesenheit von Lösungs- hzw. Verdünnungsmitteln und Anlagerungs- katalysatoren erfolgen. Vorzugsweise wird wegen der Leichtflüchtigkeit des Dimethylamins unter Druck gearbeitet. Als Anlage rungskatalysatoren benützt man vorteilhaft quaternäre Ammoniumbasen, wie z. B. Trime thylbenzylammoniumhydroxyd. The subject of the present patent is a process for the preparation of a new basic substituted fatty acid (2-halo-6methyl-anilide), which is characterized in that a compound of the formula EMI1.1 with dimet. hylamine converts. The reaction can be carried out in the presence or absence of solution. Diluents and addition catalysts take place. It is preferable to work under pressure because of the volatility of dimethylamine. As plant approximately catalysts are used advantageously quaternary ammonium bases, such as. B. Trimethylbenzylammonium hydroxide. Das so erhaltene 8-Dimethylamino-propion säure- (2-chlor-6-methyl-anilid) bildet ein fa. rbloses Öl ; dessen Hydrochlorid schmilzt bei 77, 5-79, 5 . Das neue Anilid soll als Lokal anästhetikum. und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden. The 8-dimethylamino-propionic acid (2-chloro-6-methyl-anilide) obtained in this way forms a fa. colorless oil; its hydrochloride melts at 77, 5-79, 5. The new anilide is said to be used as a local anesthetic. and as an intermediate for the production of other derivatives. Beispiel: Ein Gemisch von 20 Gewichtsteilen Acryl- säure-(2-chlor-6-methyl-anilid), 15 Gewiehts- teilen Dimethylamin und einigen Tropfen Trimethylbenzylammoniumhydroxyd wird im Autoklaven während 20 Stunden auf 145 er hitzt. Nach dem Erkalten wird durch die Reaktionsmischung Wasserdampf zwecks Entfernung flüchtiger Anteile geleitet. Anschlie- ssend wird verdampft und der Rückstand mit Petroläther ausgezogen. Man erhält so das ss Dimetjhylamino-propionsäure-(2-chlor-6-methyl-anilid) als farbloses Öl. Example: A mixture of 20 parts by weight of acrylic acid (2-chloro-6-methyl-anilide), 15 parts by weight of dimethylamine and a few drops of trimethylbenzylammonium hydroxide is heated to 145 in the autoclave for 20 hours. After cooling, water vapor is passed through the reaction mixture to remove volatile components. It is then evaporated and the residue is extracted with petroleum ether. This gives the ss dimethylamino-propionic acid (2-chloro-6-methyl-anilide) as a colorless oil. PATENTANSPRUCH : Verfahren zur Herstellung eines basisch substituierten Fettsäure-(2-ha. logen-6-methyl- anilids), dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI1.2 mit Dimethylamin umsetzt. Das so erhaltene ss-Dimethylamino-propionsäure-(2-chlor-6-me thyl-anilid) ist ein farbloses Öl ; dessen Hydrochlorid schmilzt bei 77, 5-79, 5 . Es soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. PATENT CLAIM: Process for the preparation of a basic substituted fatty acid (2-ha. Logen-6-methyl-anilide), characterized in that a compound of the formula EMI1.2 reacts with dimethylamine. The ss-dimethylamino-propionic acid (2-chloro-6-methyl-anilide) obtained in this way is a colorless oil; its hydrochloride melts at 77, 5-79, 5. It is said to be used as a local anesthetic and as an intermediate product.
CH311582D 1952-02-25 1952-02-25 Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311582A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311582T 1952-02-25
CH306512T 1952-06-08

Publications (1)

Publication Number Publication Date
CH311582A true CH311582A (en) 1955-11-30

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ID=25735181

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311582D CH311582A (en) 1952-02-25 1952-02-25 Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide).

Country Status (1)

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CH (1) CH311582A (en)

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