CH85478A - Process for the preparation of chloroethylmorphine. - Google Patents

Process for the preparation of chloroethylmorphine.

Info

Publication number
CH85478A
CH85478A CH85478DA CH85478A CH 85478 A CH85478 A CH 85478A CH 85478D A CH85478D A CH 85478DA CH 85478 A CH85478 A CH 85478A
Authority
CH
Switzerland
Prior art keywords
morphine
preparation
melts
chloroethyl
chloroethylmorphine
Prior art date
Application number
Other languages
German (de)
Inventor
Kereszty Dr Georg Von
Wolf Dr Emil
Original Assignee
Kereszty Dr Georg Von
Wolf Dr Emil
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 Kereszty Dr Georg Von, Wolf Dr Emil filed Critical Kereszty Dr Georg Von
Publication of CH85478A publication Critical patent/CH85478A/en

Links

Landscapes

  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung von     l'hloraethylnioi#pliin.            Chloraethylinorphin    war bis jetzt noch       nicht    bekannt. Es wurde nun gefunden,     dafä     mittelst eines     Arylsulfosäure-Chloraethylesters     die     Chloraethylgruppe    sich mit guter Aus  beute in das Morphin     einführen    lässt, wenn  man die     Alkaliverbindung    des Morphins mit  dem     Arylsulfosäui-e-        Cliloraetliylester    behan  delt.

   Das neue     Chloraetliylniorphin    ist für  sich therapeutisch wirksam; es bildet aber  auch einen wertvollen Ausgangskörper für  die Darstellung neuer     1 < Iorphinderivate.     



  <I>Beispiel:</I>  1     Mol.    (30     gr)    trockenes     Morphium    wird  in einer Lösung von     aiis    1     Mol.    (2,3     gr)    Na  trium in 90     gr        abs.    Alkohol dargestelltem       Aethylat    aufgelöst und bei einer Temperatur  von<B>20</B>-<B>25'</B> innerhalb     '/2-1    Stunde unter  Rühren     tropfweise    mit der     abs.    alkoholischen  Lösung von 1     131o1.        Benzolsulfosäure-Clilor-          aethylester    versetzt.

   Nach     einstündigemStehen     wird auf dem Wasserbade solange gelinde  erwärmt, bis     Phenolphtalein    keine alkalische  Reaktion zeigt. Das Trennen der neuen Base  vom an der Reaktion nicht teilgenommenen  Anteile des Morphins erfolgt nun in der bei der         Aethylinorphindarstellung        bekannten    Weise.  Das     unveränderte    Morphin kann     zurückge-          wonnen    werden.  



  Das     Chloraethylinorphin    weist einen dop  pelten Schmelzpunkt auf, es schmilzt vorerst  bei 75<B>'</B>, wird bei höherer Temperatur fest,  um bei 105  neuerdings zu schmelzen. Das  Chlorhydrat, welches mit 1     :11o1.        Wasser          kristallisiert;        schmilzt    bei 150-151 .



  Method for the preparation of l'hloraethylnioi # pliin. Until now, chloroethylinorphine was not known. It has now been found that the chloroethyl group can be introduced into the morphine with good yield by means of an aryl sulfonic acid chloroethyl ester if the alkali metal compound of morphine is treated with the aryl sulfonic acid e-clilora ethyl ester.

   The new Chloraetliylniorphin is therapeutically effective in itself; But it also forms a valuable starting point for the preparation of new 1 <Iorphine derivatives.



  <I> Example: </I> 1 mol. (30 g) dry morphine is dissolved in a solution of aiis 1 mol. (2.3 g) sodium in 90 g abs. Ethylate represented in alcohol and dissolved at a temperature of <B> 20 </B> - <B> 25 '</B> within' / 2-1 hour with stirring dropwise with the abs. alcoholic solution of 1 131o1. Benzenesulfonic acid chloroethyl ester added.

   After standing for an hour, warm the bath gently until phenolphthalein shows no alkaline reaction. The separation of the new base from the portion of the morphine which did not take part in the reaction now takes place in the manner known for the preparation of ethylinorphine. The unchanged morphine can be recovered.



  The chloroethylinorphine has a double melting point, it initially melts at 75 <B> '</B>, solidifies at a higher temperature, only to melt again at 105. The hydrochloride, which is 1: 11o1. Water crystallizes; melts at 150-151.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung von Chloraethyl- morphin, dadurch gekennzeichnet, dar Mor- phinalkali mit dem Chloraethylester einer Arylsulfosäure behandelt wird. Das Chloraethylinorphin weist einen dop pelten Schmelzpunkt auf, es schmilzt vorerst bei 75", wird bei höherer Temperatur fest um bei 105" neuerdings zii schmelzen. <B> PATENT CLAIM: </B> Process for the preparation of chloroethyl morphine, characterized in that morphine alkali is treated with the chloroethyl ester of an aryl sulfonic acid. The chloroethylinorphine has a double melting point, it initially melts at 75 ", at a higher temperature it will melt solidly around 105" recently. Das Chlorhydrat, welches mit 1 Mol: Wasser kri stallisiert, schmilzt bei 150-151". The hydrochloride, which crystallizes with 1 mole: water, melts at 150-151 ".
CH85478D 1919-03-24 1919-09-04 Process for the preparation of chloroethylmorphine. CH85478A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU85478X 1919-03-24

Publications (1)

Publication Number Publication Date
CH85478A true CH85478A (en) 1920-06-16

Family

ID=10972677

Family Applications (1)

Application Number Title Priority Date Filing Date
CH85478D CH85478A (en) 1919-03-24 1919-09-04 Process for the preparation of chloroethylmorphine.

Country Status (1)

Country Link
CH (1) CH85478A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1017618B (en) * 1953-10-15 1957-10-17 Dausse Sa Lab Process for the preparation of the morpholylaethyl ether of morphine and its salts

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1017618B (en) * 1953-10-15 1957-10-17 Dausse Sa Lab Process for the preparation of the morpholylaethyl ether of morphine and its salts

Similar Documents

Publication Publication Date Title
CH85478A (en) Process for the preparation of chloroethylmorphine.
AT88673B (en) Process for the preparation of haloethylmorphines.
DE668489C (en) Process for the preparation of 2,4-dioxo-3, 3-dialkyltetrahydropyridine-6-carboxylic acid esters or the corresponding free acids
CH85310A (en) Process for the preparation of allyl morphine.
DE351464C (en) Process for the preparation of derivatives of a hydrogenated 2-phenylquinoline-4-carboxylic acid
DE397079C (en) Process for the preparation of diarylantimony compounds
CH235954A (en) Process for the preparation of a new therapeutically effective amidine.
DE579225C (en) Process for the preparation of 3, 4, 5-trihalopyridine-2, 6-dicarboxylic acids
DE931283C (en) Process for the preparation of thiobarbituric acid derivatives
DE904896C (en) Process for the production of chloramphenicol
DE970593C (en) Process for the preparation of D-threo-1-p-nitrophenyl-2-dichloroacetamino-1,3-propanediol
AT129783B (en) Process for the preparation of 2-oxymethylbenzimidazolaric acids.
DE890047C (en) Process for the preparation of the racemic and optically active threo-2-dichloromethyl-4-chloromethyl-5- (4&#39;-nitrophenyl) -oxazoline- (2)
DE476663C (en) Process for the preparation of N-methylsulfurous acid salts of secondary aromatic-aliphatic amines
DE512723C (en) Process for the preparation of halogen-substituted aminobenzoic acid alkamine esters
DE517002C (en) Process for the preparation of o-phenolglycine amidarsic acids
AT152837B (en) Process for the preparation of 2.4-dioxo-3.3-dialkyl-1.2.3.4-tatrahydropyridines.
DE510449C (en) Process for the preparation of 6-oxybenzylamine-3-arsinic acids and their acyl derivatives
DE318803C (en) Process for the preparation of derivatives of N-acylated p-aminophenols
DE641994C (en) Process for the preparation of acyl derivatives of the dihydrofollicle hormone
DE462842C (en) Process for the preparation of derivatives of organic arsenic compounds
DE1058067B (en) Process for the preparation of choleretically active p-oxyphenylamides
DE1044821B (en) Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their offshoots
CH217232A (en) Process for the preparation of 2-methyl-4-ethoxymethyl-6-oxy-pyridine-5-carboxamide.
CH81056A (en) Process for the preparation of 2-phenylquinoline-4-carboxylic acid allyl ester