CH222484A - Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-propyl-ketone. - Google Patents

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

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Publication number
CH222484A
CH222484A CH222484DA CH222484A CH 222484 A CH222484 A CH 222484A CH 222484D A CH222484D A CH 222484DA CH 222484 A CH222484 A CH 222484A
Authority
CH
Switzerland
Prior art keywords
sep
propyl
phenyl
piperidyl
methyl
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 CH222484A publication Critical patent/CH222484A/en

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  • Hydrogenated Pyridines (AREA)

Description

  

  Verfahren zur Herstellung von     1-llethyl-4-phenyl-piperidyl-4-propyl-keton.       Gegenstand des vorliegenden Zusatzpa  tentes ist ein Verfahren zur Herstellung von       1-Methyl        -4-pheny        1-piperidyl-4-propyl-keton,     welches dadurch gekennzeichnet ist, dass man  auf     1-Methyl-4-phenyl-piperidin-4-carbon-          säurenitril        Propylmagnesiumhalogenid    ein  wirken lässt und das     entstandene        Ketimid-          zwischenprodukt    mit verdünnter Säure zer  legt.  



  Das     1-142ethy1-4-phenyl-piperidyl-4-propyl-          keton    ist ein farbloses 01 vom Kp. 160  . Es  soll für pharmazeutische Zwecke Verwen  dung finden. Das     Hydroehlorid    ist ein farb  loses Kristallpulver vom F.     115/117     .  



  <I>Beispiel:</I>  Eine     Propylma.gnesiumbromidlö.sung,    aus  61 Gewichtsteilen     Propylbromid    und 12 Ge  wichtsteilen Magnesium in 300 Gewichtstei  len Alkohol bereitet, wird zu einer Lösung  von 60 Gewichtsteilen 1-Dlethyl-4-phenyl-         piperidin-4-carbonsäurenitril    in 100 Gewichts  teilen     Toluol    zugesetzt. Die auftretende Re  aktionswärme ist nicht erheblich; nach ihrem  Abklingen wird das Gemisch auf dem Was  serbade am absteigenden Kühler erhitzt; der  Äther destilliert ab, die     Toluollösung    wird  drei Stunden bei     Wasserbadtemperatur    ge  halten.

   Die Zerlegung erfolgt durch Auf  giessen auf Eis und Verrühren mit verdünnter  Salzsäure, von der so viel anzuwenden ist, dass  kongosaure Reaktion auf die Dauer be  stehen     bleibt.    Nach Abtrennung des     Toluols     fällt man die Base durch     -Übersättigen    der  wässerigen Lösung mit Ammoniak als Öl  aus, nimmt sie in Äther auf, trocknet über       Kaliumcarbonat    und destilliert.     Kp.-    160  .  Die Base ist ein farbloses 01. Das aus der  Ätherlösung der Base mit alkoholischer Salz  säure erhältliche     Hydrochlorid    ist ein farb  loses Kristallpulver vom F.     115/117     , das  sich leicht in Wasser löst.



  Process for the preparation of 1-llethyl-4-phenyl-piperidyl-4-propyl-ketone. The present additional patent is a process for the preparation of 1-methyl -4-pheny 1-piperidyl-4-propyl-ketone, which is characterized in that 1-methyl-4-phenyl-piperidine-4-carbon Acid nitrile propyl magnesium halide allows it to act and decomposes the resulting ketimide intermediate with dilute acid.



  1-142ethy1-4-phenyl-piperidyl-4-propyl-ketone is a colorless oil with a b.p. 160. It is intended to be used for pharmaceutical purposes. The hydrochloride is a colorless crystal powder from F. 115/117.



  <I> Example: </I> A propyl magnesium bromide solution, prepared from 61 parts by weight of propyl bromide and 12 parts by weight of magnesium in 300 parts by weight of alcohol, becomes a solution of 60 parts by weight of 1-methyl-4-phenyl-piperidine-4 -carboxylic acid nitrile in 100 parts by weight of toluene added. The heat of action 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 for three hours at water bath temperature.

   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 in the long term. After the toluene has been separated off, the base is precipitated as an oil by supersaturating the aqueous solution with ammonia, taken up in ether, dried over potassium carbonate and distilled. Bp - 160. The base is a colorless 01. The hydrochloride obtainable from the ether solution of the base with alcoholic hydrochloric acid is a colorless crystal powder of F. 115/117, which dissolves easily in water.

 

Claims (1)

EMI0002.0001 PATENTANSPRUCH' <tb> Verfahren <SEP> zur <SEP> Herstellung <SEP> von <SEP> 1-lllethyl 4-pheny-1-pipei,idyl-4-propyl-leloit, <SEP> dadureh <tb> bekennzeiahnet, <SEP> dass <SEP> man <SEP> auf <SEP> 1-Methyl-4 phenyl-piperidin-4-ci-irhoirsätireiiitril <SEP> Propyl magnesiumhalogenid <SEP> einwirken <SEP> lässt <SEP> und <SEP> das <tb> entstandene <SEP> Ketimidzwisehenprodukt <SEP> mit verdünnter Säure zerlegt. EMI0002.0002 Das <SEP> 1-Afethy <SEP> 1-4-plienyl-piperidyl-4-propyl keton <SEP> ist <SEP> ein <SEP> farbloses <SEP> 01 <SEP> vom <SEP> Kp;, <SEP> 160 <SEP> . <SEP> Das <tb> Hydroehlorid <SEP> ist <SEP> ein <SEP> farbloses <SEP> Kristallpulver <tb> vom <SEP> F. <SEP> 115/117 <SEP> . EMI0002.0001 PATENT CLAIM ' <tb> Process <SEP> for the <SEP> production <SEP> of <SEP> 1-lllethyl 4-pheny-1-pipei, idyl-4-propyl-leloit, <SEP> dadureh <tb> declares, <SEP> that <SEP> is <SEP> <SEP> allowed to act <SEP> on <SEP> 1-methyl-4 phenyl-piperidine-4-ci-irhoirsätireiiitril <SEP> propyl magnesium halide <SEP> and <SEP> that <tb> resulting <SEP> ketimide bond product <SEP> decomposed with dilute acid. EMI0002.0002 The <SEP> 1-Afethy <SEP> 1-4-plienyl-piperidyl-4-propyl ketone <SEP> is <SEP> a <SEP> colorless <SEP> 01 <SEP> from <SEP> Kp ;, <SEP > 160 <SEP>. <SEP> That <tb> Hydrochloride <SEP> is <SEP> a <SEP> colorless <SEP> crystal powder <tb> from <SEP> F. <SEP> 115/117 <SEP>.
CH222484D 1939-03-30 1940-03-30 Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-propyl-ketone. CH222484A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE222484X 1939-03-30
CH218517T 1940-03-30

Publications (1)

Publication Number Publication Date
CH222484A true CH222484A (en) 1942-07-15

Family

ID=25726171

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222484D CH222484A (en) 1939-03-30 1940-03-30 Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-propyl-ketone.

Country Status (1)

Country Link
CH (1) CH222484A (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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