CH112746A - Process for the preparation of d-y-Benzoylecgonyl chloride. - Google Patents

Process for the preparation of d-y-Benzoylecgonyl chloride.

Info

Publication number
CH112746A
CH112746A CH112746DA CH112746A CH 112746 A CH112746 A CH 112746A CH 112746D A CH112746D A CH 112746DA CH 112746 A CH112746 A CH 112746A
Authority
CH
Switzerland
Prior art keywords
chloride
preparation
benzoylecgonyl
forms
alcohols
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 CH112746A publication Critical patent/CH112746A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine

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

Description

  

      Yerfahren    zur Darstellung von     d-^f-Benzoyleegonylehlorid.       Nach dem Verfahren des Hauptpatentes  wird     1-Benzoyleegonylchlorid    dadurch ge  wonnen, dass man Säurechloride, wie     Thionyl-          chlorid,        Phosphorpentachlorid,    auf     1-Benzoyl-          ecgonin    einwirken lässt.  



  Es wurde gefunden, dass sich dieses  Darstellungsverfahren auch für die Gewinnung  von     d-@;-Benzoyleegonylehlorid    anwenden lässt.  Durch Einwirkung vorn Säurechloriden, wie       Thionylchlorid,        Phosphorpentachlorid,    auf       d-Z-Benzoyleegonin    erhält     inan    das salzsaure       d--"-Berizoyleegonylchlorid    in Form einer  weissen Masse, die leicht     pulverisierbar    ist.  Übergiesst man dieses Salz mit Alkoholen,  so entstehen in nahezu quantitativer Ausbeute  die entsprechenden Ester.

   Das     d-v-Benzoyl-          ecgonylchlorid    bildet ein Ausgangsprodukt  für die Herstellung von therapeutisch wert  vollen Estern des     d--v-Benzoyleegonins.     



  <I>Beispiel:</I>  20 Teile trockenes     d-@L-Benzoyleegoriiri     werden in einem geeigneten, mit     RückflulI-          kühler    versehenen Gefäss mit 60-80 Teilen       Thionylchlorid    versetzt. Dann erwärmt man  langsam im Wasserbad auf<B>75-800</B> und  hält die Temperatur auf dieser Höhe, bis  sich alles     d-@L-Benzoylecgonin    gelöst hat.  Man destilliert das überschüssige Thionyl-         chlorid    im Vakuum bei zirka 40   ab. Das  salzsaure     d-v-Berizoyleegoriylchlorid    hinter  bleibt in Form einer festen weissen Masse,  welche bei zirka 163   unter Zersetzung  schmilzt.

   Zur Charakterisierung kann man  dieses Chlorid mit Alkoholen     (Methyl-,        Äthyl-,          Allylalkohol        etc.)    verestern und erhält so  die entsprechenden     d-@,-Benzoyleegoninestei-.     So wurde zum Beispiel durch Behandeln des  Chlorids mit Methylalkohol     d-%.-Cocaiin    vom  Schmelzpunkt 45-46  erhalten, und zwar in  einer     Ausbeute    von 92      /o.  



      Method for the preparation of d- ^ f-Benzoyleegonylehlorid. According to the process of the main patent, 1-benzoyleegonyl chloride is obtained by letting acid chlorides such as thionyl chloride and phosphorus pentachloride act on 1-benzoyl ecgonine.



  It has been found that this preparation method can also be used for the production of d - @; - Benzoyleegonyl chloride. By the action of acid chlorides, such as thionyl chloride, phosphorus pentachloride, on dZ-benzoyleegonine, the hydrochloric acid d- "- berizoyleegonyl chloride is obtained in the form of a white mass that can easily be pulverized. If this salt is poured over with alcohols, the corresponding results are obtained in almost quantitative yield Ester.

   The d-v-benzoyl-ecgonyl chloride forms a starting product for the production of therapeutically valuable esters of d-v-benzoyleegonine.



  <I> Example: </I> 20 parts of dry d- @ L-Benzoyleegoriiri are mixed with 60-80 parts of thionyl chloride in a suitable vessel equipped with a reflux cooler. Then slowly warm up to <B> 75-800 </B> in a water bath and keep the temperature at this level until all of the d- @ L-benzoylecgonine has dissolved. The excess thionyl chloride is distilled off in vacuo at approx. The hydrochloric acid d-v-berizoyleegoriyl chloride behind remains in the form of a solid white mass, which melts at about 163 with decomposition.

   For characterization, this chloride can be esterified with alcohols (methyl, ethyl, allyl alcohol, etc.) and thus the corresponding d - @, - Benzoyleegoninestei- is obtained. For example, by treating the chloride with methyl alcohol, d% cocaine with a melting point of 45-46 was obtained in a yield of 92%.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von d-1',-Ben- zoylecgonylchlorid, dadurch gekennzeichnet, dass man auf d-v-Berizoyleegoriin Säurechloride einwirken lässt. Das salzsaure d--Benzoylecgonylchlorid _ bildet eine leicht pulverisierbare Masse, welche beim Versetzen mit Alkoholen in nahezu quantitativer Ausbeute die ent sprechenden Ester liefert. Es bildet ein Ausgangsprodukt für die Herstellung vorn therapeutisch wertvollen Estern des d-v-Beri- zoylecgonins. PATENT CLAIM: Process for the preparation of d-1 ', - benzoylecgonyl chloride, characterized in that acid chlorides are allowed to act on d-v-berizoyleegoriin. The hydrochloric acid d-Benzoylecgonylchlorid _ forms an easily pulverizable mass which, when mixed with alcohols, gives the corresponding esters in almost quantitative yield. It forms a starting product for the production of therapeutically valuable esters of d-v-berizoylecgonine.
CH112746D 1924-07-05 1925-05-15 Process for the preparation of d-y-Benzoylecgonyl chloride. CH112746A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH111994T 1924-07-05
CH112746T 1925-05-15

Publications (1)

Publication Number Publication Date
CH112746A true CH112746A (en) 1925-11-16

Family

ID=25707963

Family Applications (1)

Application Number Title Priority Date Filing Date
CH112746D CH112746A (en) 1924-07-05 1925-05-15 Process for the preparation of d-y-Benzoylecgonyl chloride.

Country Status (1)

Country Link
CH (1) CH112746A (en)

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