CH222731A - Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-ethyl-ketone. - Google Patents

Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-ethyl-ketone.

Info

Publication number
CH222731A
CH222731A CH222731DA CH222731A CH 222731 A CH222731 A CH 222731A CH 222731D A CH222731D A CH 222731DA CH 222731 A CH222731 A CH 222731A
Authority
CH
Switzerland
Prior art keywords
phenyl
piperidyl
methyl
ethyl
ketone
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie 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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH222731A publication Critical patent/CH222731A/en

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Description

  

  Verfahren zur Herstellung von     1-lliethyl-4-phenyl-piperidyl-4-äthyl-keton.       Gegenstand des vorliegenden Zusatz  patentes ist ein Verfahren zur Herstellung  von     1-Methyl-4-phenyl-piperidyl-4-äthyl-          keton,    welches dadurch gekennzeichnet ist,  dass man auf     1-Methyl-4-phenyl-piperidin-4-          carbonsäurenitril        Äthylmagnesiumhalogenid     einwirken lässt und das entstandene     Ketimid-          zwischenprodukt    mit verdünnter     Säure    zer  legt.  



  Das     1-1#Iethyl-4-phenyl-piperidyl-4-äthyl-          keton    ist ein farbloses 01 vom     Kp3    145'. Es  bildet mit Mineralsäuren in Wasser leicht  lösliche Salze. Das Hydrochlorid ist ein farb  loses     Kristallpulver    vom F.170 . Es dient  als     Spasmolyticum    und     Analgeticum.     



  <I>Beispiel:</I>  Eine     Äthylmagnesiumbromidlösung,    aus  55 Gewichtsteilen     Äthylbromid    und 12 Ge  wichtsteilen Magnesium in 200 Gewichts  teilen Äther bereitet, wird zu einer Lösung  von 80 Gewichtsteilen     1-Methyl-4-phenyl-          piperidin-4-carbonsäurenitril    in 200 Ge-         wichtsteilen        Toluol    zugesetzt. Die auf  tretende Reaktionswärme ist nicht erheblich;  nach ihrem Abklingen wird das     Gemisch    auf  dem Wasserbade am absteigenden Kühler  erhitzt; der Äther destilliert ab, die     Toluol-          lösung    wird drei Stunden bei Wasserbad  temperatur gehalten.

   Die Zerlegung erfolgt       durch    Aufgiessen auf Eis     und    Verrühren mit  verdünnter Salzsäure, von der soviel anzu  wenden ist, dass kongosaure     Reaktion    auf die  Dauer bestehen bleibt. Nach Abtrennung des       Toluols    fällt man die Base durch     Über-          sättigen    der     wässrigen    Lösung mit Ammoniak  als Öl     aus,    nimmt sie in Äther auf, trocknet  über     Kaliumcarbonat    und destilliert.     Kp3     145'. Die Base ist     ein    farbloses 01.

   Das  Hydrochlorid     ist    ein farbloses     Kristallpulver     vom F.<B>170',</B> es löst sich leicht in Wasser.



  Process for the preparation of 1-lliethyl-4-phenyl-piperidyl-4-ethyl-ketone. The subject of the present additional patent is a process for the production of 1-methyl-4-phenyl-piperidyl-4-ethyl-ketone, which is characterized in that 1-methyl-4-phenyl-piperidine-4-carboxylic acid nitrile is acted on by ethylmagnesium halide and the resulting ketimide intermediate decomposes with dilute acid.



  The 1-1 # Iethyl-4-phenyl-piperidyl-4-ethyl-ketone is a colorless oil of bp3 145 '. It forms salts that are easily soluble in water with mineral acids. The hydrochloride is a colorless crystal powder from F.170. It serves as a spasmolytic and analgesic.



  <I> Example: </I> An ethylmagnesium bromide solution, prepared from 55 parts by weight of ethyl bromide and 12 parts by weight of magnesium in 200 parts by weight of ether, becomes a solution of 80 parts by weight of 1-methyl-4-phenyl-piperidine-4-carboxylic acid nitrile in 200 Parts by weight of toluene added. The heat of reaction occurring is not significant; After they have subsided, the mixture is heated on the water bath on the descending cooler; the ether distills off, the toluene solution is kept at water bath temperature for three hours.

   It is broken down by pouring it onto ice and stirring it with dilute hydrochloric acid, of which so much must be used that the Congo acidic reaction persists over time. After the toluene has been separated off, the base is precipitated as an oil by over-saturating the aqueous solution with ammonia, taken up in ether, dried over potassium carbonate and distilled. Kp3 145 '. The base is a colorless 01.

   The hydrochloride is a colorless crystal powder from F. <B> 170 ', </B> it dissolves easily in water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 1-ll2ethyl- 4-phenyl-piperidyl-4-äthylketon, dadurch ge kennzeichnet, dass man auf 1-Methyl-4- phenyl-piperidin-4-carbonsäurenitril Äthy1- magnesiumhalogenid einwirken lässt und das entstandene Ketimidzwischenprodukt mit verdünnter Säure zerlegt. Das 1-Methyl-4-phenyl-piperidyl-4-äthyl- keton ist ein farbloses<B>01</B> vom Kp3 145'. Es bildet mit Mineralsäuren in Wasser leicht lösliche Salze. PATENT CLAIM: A process for the preparation of 1-ll2ethyl-4-phenyl-piperidyl-4-ethyl ketone, characterized in that 1-methyl-4-phenyl-piperidine-4-carboxylic acid nitrile is allowed to act on ethyl magnesium halide and the resulting ketimide intermediate product with diluted acid decomposed. The 1-methyl-4-phenyl-piperidyl-4-ethyl ketone is a colorless <B> 01 </B> with bp3 145 '. It forms salts that are easily soluble in water with mineral acids. Das Hydrochlorid ist ein farb loses Kristallpulver vom F.<B>170'.</B> Es dient als Spasmolyticum und Analgeticum. The hydrochloride is a colorless crystal powder from F. <B> 170 '. </B> It is used as a spasmolytic and analgesic.
CH222731D 1939-03-30 1940-03-30 Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-ethyl-ketone. CH222731A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE222731X 1939-03-30
CH218517T 1940-03-30

Publications (1)

Publication Number Publication Date
CH222731A true CH222731A (en) 1942-07-31

Family

ID=25726173

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222731D CH222731A (en) 1939-03-30 1940-03-30 Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-ethyl-ketone.

Country Status (1)

Country Link
CH (1) CH222731A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2486796A (en) * 1943-06-25 1949-11-01 Ciba Pharm Prod Inc Esters of 1-alkyl-4-hydroxyphenylpiperidyl-4-ketones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2486796A (en) * 1943-06-25 1949-11-01 Ciba Pharm Prod Inc Esters of 1-alkyl-4-hydroxyphenylpiperidyl-4-ketones

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