DE421387C - Process for the preparation of pure ª ‡ -sparteine iodomethylate - Google Patents

Process for the preparation of pure ª ‡ -sparteine iodomethylate

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Publication number
DE421387C
DE421387C DEM86102D DEM0086102D DE421387C DE 421387 C DE421387 C DE 421387C DE M86102 D DEM86102 D DE M86102D DE M0086102 D DEM0086102 D DE M0086102D DE 421387 C DE421387 C DE 421387C
Authority
DE
Germany
Prior art keywords
sparteine
pure
iodomethylate
preparation
chloroform
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEM86102D
Other languages
German (de)
Inventor
Dr Amadeus Duetzmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CHEM FAB
Merck KGaA
Original Assignee
CHEM FAB
E Merck 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 CHEM FAB, E Merck AG filed Critical CHEM FAB
Priority to DEM86102D priority Critical patent/DE421387C/en
Application granted granted Critical
Publication of DE421387C publication Critical patent/DE421387C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Description

Verfahren zur Darstellung von reinem a-Sparteinjodmethylat. Bisher ist in den Arbeiten von M o u r e u und V a 1 e u r über Spartein (C. r. 154 [191z], Seite 3o9) beobachtet worden, daß das Spartein zwei stereoisomere jodmethylate (von den Autoren mit a und a' bezeichnet) bildet und daß durch Umkristallisieren aus Wasser sich schließlich ein bestinuntes, einheitliches jo-dmethylat gewinnen läßt.Process for the preparation of pure α-sparteine iodine methylate. Until now is in the work of M o u r e u and V a 1 e u r on Sparteine (C. r. 154 [191z], Page 309) it has been observed that the sparteine contains two stereoisomeric iodomethylates (from the authors designated with a and a ') and that by recrystallization Water can finally obtain a determined, uniform jo-dmethylate.

Diese Art der Reinigung ist natürlich mit großen Verlusten verbunden, indem die Kristallisationsfähigkeit des reinen jodmethylats durch die Beimengung des Isomeren sehr ungünstig beeinflußt wird, ein Umstand, der bei der Kostspieligkeit des Rohstoffes sehr ins Gewicht fällt.This type of cleaning is of course associated with great losses, by increasing the crystallizability of the pure iodine methylate through the admixture of the isomer is very adversely affected, a circumstance which is due to the cost of the raw material is very important.

Es wurde nun die überraschende Beobachtung gemacht, daß das a-Jodmethylat eine außerordentlich starke Neigung zur Bildung einer Kristalichloroformverbindung zeigt, eine Neigung, die beispielsweise so groß ist, daß beim Übergießen :eines Gemenges beider Jodmethylate mit Chloroform eine starke Erwärmung auftritt und ferner einer wässerigen Lösung des jodmethylats durch Ausschütteln. mit Chloroform das Salz restlos entzogen wird.The surprising observation has now been made that the α-iodomethylate an extremely strong tendency to form a crystal chloroform compound shows a tendency which is so great, for example, that when pouring over: one Mixture of both iodine methylates with chloroform a strong warming occurs and furthermore an aqueous solution of the iodomethylate by shaking. with chloroform that Salt is completely removed.

Beispiel. 330 g rohes Sparteinjodmethylat (hergestellt aus 2159 Sparteinbase, 26o g Methyljodid und 275 ccm Essigester) wird durch Erwärmen mit dem doppelten, Volumen Chloroform völlig gelöst und noch heiß etwa das gleiche Volumen heißer Essigester auf einmal unter Umschwenken zugesetzt. Sofort erstarrt alles zu einem Kristallkuchen. Nach eintägigem Stehen wird abfiltriert, mit Chloroform-Essigester (in. obigem Verhältnis) nachgewaschen und an der Luft getrocknet. Die Ausbeute beträgt 225g. Dieses Produkt wird mit 15o ccm Wasser auf dem Wasserbade bis zur Lösung erwärmt und einige Minuten bis zum Verschwinden des Chloroforms gekocht. Beim Erkalten kristallisieren 195g völlig reines einheitliches a-Jodmethylat in großen, derben Würfeln.Example. 330 g of crude sparteine iodine methylate (made from 2159 sparteine base, 26o g methyl iodide and 275 ccm ethyl acetate) is completely dissolved by heating with twice the volume of chloroform and while still hot, about the same volume of hot ethyl acetate is added at once while swirling. Immediately everything solidifies into a crystal cake. After standing for one day, it is filtered off, washed with chloroform / ethyl acetate (in the above ratio) and air-dried. The yield is 225g. This product is heated with 150 cc of water on the water bath until it dissolves and boiled for a few minutes until the chloroform disappears. On cooling, 195g of completely pure, uniform α-iodine methylate crystallize in large, coarse cubes.

Die a-Jodmethylat-Chloroforniverbmdung schmilzt bei 236 bis 238° C. Sie enthält Mol. Kristallchloroform, ist in kaltem Wasser sehr wenig löslich, schwer löslich in. Essigester, sehr leicht löslich in Alkohol und Äther.The α-iodomethylate chloroform compound melts at 236 to 238 ° C. It contains mol. Of crystal chloroform, is very sparingly soluble in cold water, sparingly soluble in ethyl acetate, very easily soluble in alcohol and ether.

Das in der Chloroform-Mutterlauge gelöste a'-Jodmethylat wird durch Einengen und Kristallisieren chloroformfrei gewonnen. Die Ausbeute beträgt etwa 3o g a'-Sparteinjodmethylat.The a'-iodine methylate dissolved in the chloroform mother liquor is through Concentration and crystallization obtained free of chloroform. The yield is about 3o g of a'-sparteine iodine methylate.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von reinem a-Sparteinjodmethylat, dadurch gekennzeichnet, daß man aus dem rohen Gemisch der isomeren jodmethylate das a-Jodmethylat als Kristallchloroformverbindung abscheidet.PATENT CLAIM: Process for the preparation of pure a-sparteiniodomethylate, characterized in that one from the crude mixture of isomeric iodomethylates the α-iodine methylate separates out as a crystal chloroform compound.
DEM86102D 1924-08-23 1924-08-23 Process for the preparation of pure ª ‡ -sparteine iodomethylate Expired DE421387C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEM86102D DE421387C (en) 1924-08-23 1924-08-23 Process for the preparation of pure ª ‡ -sparteine iodomethylate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEM86102D DE421387C (en) 1924-08-23 1924-08-23 Process for the preparation of pure ª ‡ -sparteine iodomethylate

Publications (1)

Publication Number Publication Date
DE421387C true DE421387C (en) 1925-11-11

Family

ID=7320383

Family Applications (1)

Application Number Title Priority Date Filing Date
DEM86102D Expired DE421387C (en) 1924-08-23 1924-08-23 Process for the preparation of pure ª ‡ -sparteine iodomethylate

Country Status (1)

Country Link
DE (1) DE421387C (en)

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