CH306505A - Process for the preparation of a new local anesthetic. - Google Patents

Process for the preparation of a new local anesthetic.

Info

Publication number
CH306505A
CH306505A CH306505DA CH306505A CH 306505 A CH306505 A CH 306505A CH 306505D A CH306505D A CH 306505DA CH 306505 A CH306505 A CH 306505A
Authority
CH
Switzerland
Prior art keywords
preparation
ether
local anesthetic
new local
hydrochloric acid
Prior art date
Application number
Other languages
German (de)
Inventor
Hofstetter Emil
Original Assignee
Geistlich Soehne 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 Geistlich Soehne Ag filed Critical Geistlich Soehne Ag
Publication of CH306505A publication Critical patent/CH306505A/en

Links

Classifications

    • 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

Landscapes

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

Description

  

  



  Verfahren zur Herstellung eines neuen LokalanÏsthetikums. ?
Vorliegende Erfindung betrifft ein Verfahren zur Herstellung von ¯-DiÏthylamino-nbuttersÏureanilid der Formel
EMI1.1     

Es   morde    gefunden, dass diese bisher noeh   nichtbekannteVerbindunginteressante    phar  makologische Eigensehaften, insbesond. ere    eine dem Procain Ïhnliche, anÏsthesierende Wir  kung besitzt.   



   Die Herstellung dieser Verbindung erfolgt erfindungsgemäss durch Umsetzung von Crotonsäureanilid mit   Diäthyla. min.    Die Reaktion verläuft wie folgt :
EMI1.2     

Zweckmässig führt man die Rea. ktion in    geschlossenem Gefäss während einigen Stun-    den bei   100-150  C durch. Da. bei    kann man in An-oder Abwesenheit von   Losungsmitteln    arbeiten Durch Versetzen des Reaktionsgemisehes mit verdünnter SÏure; insbesondere Salzsäure, kann man die entstande neue Verbindung von eventuell noch vorhandenem Aus  gangsmaterial    trennen, da letzteres im   Gegen-    satz zur neuen Verbindung in verdünnter SalzsÏure sehwer-bis unlöslich ist.



   Beispiel :
29 Teile Crotonsäureanilid und 70 Teile Diäthylamin werden zusammen während 18 Stunden im   geschlossenen Gefä. ss auf    120 bis   130     C erhitzt. Danach wird der   Diäthylamin-    überschuss abdestilliert. Danach wird mit Was ser verdünnt und mit Salzsäure angesÏuert.



  Vom ungelösten Material wird getrennt und alkalisch gestellt. Die   dadurchausgefallene    halbfeste Verbindung wird in Äther aufgenommen. Nach dem Trocknen wird der Äther abdestilliert und der   Rüekstand    aus Petrol. äther umkristallisiert.



   Das ¯-DiÏthylaminobuttersÏureanilidschmilzt bei   4W46       C,    es ist in der berechneten Menge Salzsäure leicht   loslich.    Ferner ist es in Alko  hol, Äther und    Benzol ebenfalls leicht   loslich,    aus Petroläther ist das Anilid umkristallisierbar. Smp. des Hydrochlorids 132-134¯ C.



  



  Process for the production of a new local anÏesthetic. ?
The present invention relates to a process for the preparation of ¯-DiÏthylamino-nbuttersÏureanilid of the formula
EMI1.1

Murder found that this previously unknown compound has interesting pharmacological properties, in particular ere has an anesthetic effect similar to procaine.



   According to the invention, this compound is produced by reacting crotonic acid anilide with diethyla. min. The reaction goes as follows:
EMI1.2

The Rea. ction in a closed vessel for a few hours at 100-150 C. There. at you can work in the presence or absence of solvents by adding dilute acid to the reaction mixture; In particular hydrochloric acid, the resulting new compound can be separated from any starting material that may still be present, since the latter, in contrast to the new compound, is difficult to insoluble in dilute hydrochloric acid.



   Example:
29 parts of crotonic acid anilide and 70 parts of diethylamine are kept together for 18 hours in a closed vessel. ss heated to 120 to 130 C. The excess diethylamine is then distilled off. Then it is diluted with water and acidified with hydrochloric acid.



  The undissolved material is separated and made alkaline. The semi-solid connection that has failed is taken up in ether. After drying, the ether is distilled off and the residue is petrol. ether recrystallized.



   The ¯-diethylaminobutyric acid anilide melts at 4W46 C and is easily soluble in the calculated amount of hydrochloric acid. It is also easily soluble in alcohol, ether and benzene, and the anilide can be recrystallized from petroleum ether. M.p. of the hydrochloride 132-134¯ C.

Claims (1)

PATENTANSPRUCH : Verfahren zur Herstellung von 3-Diäthvl- amino-n-buttersÏureanilid, dadurch gekennzeichnet, dat man n CrotonsÏureanilid mit Di äthylamin umsetzt. PATENT CLAIM: Process for the preparation of 3-diethvl amino-n-buttersureanilid, characterized in that one reacts dat n CrotonsÏureanilid with diethylamine. Die neue Verbindung schmilzt bei 45 bis 46 C ; sie ist in der berechneten Menge Salzsäure leicht loslieh. Ferner ist sie in Alkohol, Äther und Benzol ebenfalls leicht loslich ; aus Petroläther ist das Anilid umkristallisierbar. The new compound melts at 45 to 46 C; it is easy to get loose in the calculated amount of hydrochloric acid. It is also easily soluble in alcohol, ether, and benzene; the anilide can be recrystallized from petroleum ether. Smp. des Hydroehlorids 132-134¯ C. M.p. of the hydrochloride 132-134¯ C. UNTERANSPRÜCHE : 1. Verfahren nach Patentansprueh, dadurch gekennzeichnet, dass man in Gegenwart eines Lösungsmittels arbeitet. SUBCLAIMS: 1. The method according to patent claim, characterized in that one works in the presence of a solvent. 2. Verfahren nach Patentanspruch und Unteranspruch l, dadurch gekennzeichnet, dass man im gesehlossenen Gefäss mehrere Stunden auf 100-150 C erhitzt. 2. The method according to claim and dependent claim l, characterized in that it is heated to 100-150 C for several hours in the closed vessel.
CH306505D 1952-05-13 1952-05-13 Process for the preparation of a new local anesthetic. CH306505A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH306505T 1952-05-13

Publications (1)

Publication Number Publication Date
CH306505A true CH306505A (en) 1955-04-15

Family

ID=4492841

Family Applications (1)

Application Number Title Priority Date Filing Date
CH306505D CH306505A (en) 1952-05-13 1952-05-13 Process for the preparation of a new local anesthetic.

Country Status (1)

Country Link
CH (1) CH306505A (en)

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