CH153686A - Process for the preparation of l-phenylpropanolphenylbutanone methylamine. - Google Patents

Process for the preparation of l-phenylpropanolphenylbutanone methylamine.

Info

Publication number
CH153686A
CH153686A CH153686DA CH153686A CH 153686 A CH153686 A CH 153686A CH 153686D A CH153686D A CH 153686DA CH 153686 A CH153686 A CH 153686A
Authority
CH
Switzerland
Prior art keywords
ephedrine
methylamine
preparation
bromobutyrophenone
phenylpropanolphenylbutanone
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH153686A publication Critical patent/CH153686A/en

Links

Description

  

  Verfahren zur Darstellung von     1-Phenylpropanolphenylbutanonmethylamin.       Es wurde gefunden,     dass    sich     1-Ephedrin     mit     a-Brombutyrophenon    leicht gemäss nach-    stehender Gleichung zu     1-Phenylpropanolphe-          nylbutanonmethylamin    umsetzt:  
EMI0001.0007     
    Die Umsetzung kann dadurch mit guter  Ausbeute erreicht werden,     dass    man einen       Überschussvon        1-Ephedrin        mita-Brombutyro-          phenon    zusammenbringt.

   Statt einen     Über-          schuss    von     1-Ephedrin    zu verwenden, kann  man die Kondensation mit Alkali bewirken.  



  Das     1.Phenylpropanolphenylbutanonmethyl-          amin    ist bei gewöhnlicher- Temperatur ölig.       In    den üblichen organischen Lösungsmitteln,  wie Alkohol, Äther, Benzol, Chloroform, ist  die Verbindung leicht löslich, in Wasser  schwer löslich. Mit Säure bildet die Verbin  dung in Wasser lösliche Salze.  



  Die neue Verbindung soll als solche thera  peutische Verwendung finden oder als Zwi-         schenproduktzurHerstellungpharrnazeutischer     Präparate dienen.    <I>Beispiel:</I>    <B>5</B> Teile     1-Ephedrinhydrochlorid    werden  fünf Stunden mit 20 Teilen Wasser und 20  Teilen Benzol mit<B>5,5</B> Teilen     a-Brombutyro-          phenon    und<B>2,8</B> Teilen     Ätzkali    gekocht.  Dann werden die Basen in verdünnter Salz  säure aufgenommen, mit Ammoniak gefällt,  wieder in verdünnter Salzsäure gelöst und  nochmals mit Ammoniak gefällt. Der Nieder  schlag wird in Äther gelöst.

   Den Ätherrück  stand löst man in der berechneten Menge  verdünnter Salzsäure und erhält so eine      Lösung des salzsauren Kondensationsproduk  tes. Die Base selbst ist ölig.



  Process for the preparation of 1-phenylpropanolphenylbutanone methylamine. It was found that 1-ephedrine reacts easily with a-bromobutyrophenone to give 1-phenylpropanolphenylbutanone methylamine according to the following equation:
EMI0001.0007
    The reaction can be achieved in good yield by combining an excess of 1-ephedrine with a-bromobutyrophenone.

   Instead of using an excess of 1-ephedrine, the condensation can be brought about with alkali.



  The 1st phenylpropanolphenylbutanonemethylamine is oily at ordinary temperature. The compound is easily soluble in the usual organic solvents such as alcohol, ether, benzene, chloroform, and sparingly soluble in water. With acid, the compound forms water-soluble salts.



  The new compound is intended to find therapeutic use as such or to serve as an intermediate product for the production of pharmaceutical preparations. <I> Example: </I> <B> 5 </B> parts of 1-ephedrine hydrochloride are mixed with 20 parts of water and 20 parts of benzene with <B> 5.5 </B> parts of a-bromobutyrophenone and for five hours <B> 2.8 </B> parts cooked caustic potash. Then the bases are taken up in dilute hydrochloric acid, precipitated with ammonia, redissolved in dilute hydrochloric acid and precipitated again with ammonia. The precipitate is dissolved in ether.

   The ether residue is dissolved in the calculated amount of dilute hydrochloric acid and a solution of the hydrochloric acid condensation product is obtained. The base itself is oily.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung von 1-Phenyl- pi-opanolphenylbutanonmethylamin, dadurch gekennzeichnet, dass man 1-Ephedrin und a- Brombutyrophenon aufeinander einwirken lässt. Das 1-Phenylpi-opanolpheriylbtitanonmethyl- amin ist bei gewöhnlicher Temperatur ölig. In den üblichen organischen Lösungsmitteln, wie Alkohol, Äther, Benzol, Chloroform, ist die Verbindung leicht löslich, in Wasser schwer löslich. Mit Säure bildet die Verbin dung in Wasser lösliche Salze. <B> PATENT CLAIM: </B> Process for the preparation of 1-phenyl-pi-opanolphenylbutanone-methylamine, characterized in that 1-ephedrine and α-bromobutyrophenone are allowed to act on one another. 1-Phenylpi-opanolpheriylbtitanonmethyl- amine is oily at normal temperature. The compound is easily soluble in the usual organic solvents such as alcohol, ether, benzene, chloroform, and sparingly soluble in water. With acid, the compound forms water-soluble salts. Die neue Veibindung soll als solche thera peutische Verwendung finden oder als Zwi- schenproduktztii-Herstellungpharmazeutischer Präparate dienen. UNTERANSPRüCHE: <B>1.</B> Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man einen Überschuss von 1-Ephedrin verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Einwirkung von 1-Ephedrin auf a-Brombutyrophenon in Gegenwart von Alkali vornimmt. The new connection is intended to find therapeutic use as such or serve as an intermediate product in the manufacture of pharmaceutical preparations. SUBClaims: <B> 1. </B> Method according to patent claim, characterized in that an excess of 1-ephedrine is used. 2. The method according to claim, characterized in that the action of 1-ephedrine on a-bromobutyrophenone is carried out in the presence of alkali.
CH153686D 1930-01-18 1930-12-10 Process for the preparation of l-phenylpropanolphenylbutanone methylamine. CH153686A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE153686X 1930-01-18
DE210230X 1930-02-21
DE260630X 1930-06-26
CH150921T 1930-12-10

Publications (1)

Publication Number Publication Date
CH153686A true CH153686A (en) 1932-03-31

Family

ID=27429599

Family Applications (1)

Application Number Title Priority Date Filing Date
CH153686D CH153686A (en) 1930-01-18 1930-12-10 Process for the preparation of l-phenylpropanolphenylbutanone methylamine.

Country Status (1)

Country Link
CH (1) CH153686A (en)

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