CH240363A - Process for the preparation of N- (y, y-diphenyl-allyl) -piperidine. - Google Patents

Process for the preparation of N- (y, y-diphenyl-allyl) -piperidine.

Info

Publication number
CH240363A
CH240363A CH240363DA CH240363A CH 240363 A CH240363 A CH 240363A CH 240363D A CH240363D A CH 240363DA CH 240363 A CH240363 A CH 240363A
Authority
CH
Switzerland
Prior art keywords
diphenyl
piperidine
allyl
preparation
piperidino
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 CH240363A publication Critical patent/CH240363A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Description

  

  Verfahren zur Herstellung von     N-(r,r-Diphenyl-allyl)-piperidin.       Gegenstand der vorliegenden Erfindung  ist ein Verfahren zur Herstellung von     N-(y,y-          Diphenyl-allyl)-piperidin,    das dadurch ge  kennzeichnet ist, dass man einen     fl-Piperidino-          propionsäureester    mit einem     Phenylmagne-          siumhalogenid    umsetzt und aus dem so erhal  tenen     y-Piperidino-a,a-diphenyl-propanol-(a)     Wasser abspaltet.

      Die neue     Verbindung    ist ein in     Petrol-          äther    leicht lösliches Öl, das ein Hydrochlorid  vom F. 204-206  bildet. Sie soll als Heil  mittel sowie für die Herstellung von Heil  mitteln verwendet werden.

           Beispiel:     Zu einer     Phenylmagnesiumbromidlösung     aus 157 Gewichtsteilen Brombenzol und 24  Gewichtsteilen Magnesium in 300     cm3    Äther  werden 72     Gewichtsteile        P-Piperidinopro-          pionsäure-n-butylester,        gp"        137-138     der  Formel  
EMI0001.0020     
         zutropfen    gelassen. Es tritt dabei Selbst  erwärmung auf, die die Ätherlösung im Sie  den hält. Nach beendigtem     Zutropfen    wird  das Gemisch noch zwei     Stunden    unter Rück  fluss gekocht.

   Darauf wird es unter Rühren  in     eine    Mischung von 200     Raumteilen     37 %     iger    Salzsäure     und    800     Gewichtsteilen     Eis eingegossen. Das sich dabei abscheidende  Hydrochlorid des     y-Piperidino-a,a-diphenyl-          propanol-(a)    der Formel  
EMI0001.0031     
    wird abgesaugt, mit Äther, darauf mit etwas  verdünnter Salzsäure, dann     wieder        mit    Äther           ausgewaschen    und im     Vakuumexsikllator     über     Natriumhydroxyd    getrocknet.  



  Das Produkt     ist    ein farbloses Kristall  pulver vom F. 216  unter Zersetzung, ziem  lich wenig löslich in kaltem, leichter löslich  in heissem Wasser,     umkristallisierbar    aus Al  kohol. Die Base ist ein farbloses     kristalli-          sches    Pulver vom F. 119-120 .  



  Zur Wasserabspaltung löst man zweck  mässig die Base in der dreifachen Menge  85 ö     iger    Phosphorsäure und erhitzt 1 Stunde  auf     180-140 .    Durch Ausfällen mit Natron  lauge erhält man das ölige     N-(y,y-Diphenyl-          allyl)-piperidin    der Formel  
EMI0002.0012     
    das in Äther aufgenommen, abgetrennt und  mittels alkoholischer Salzsäure in das     Hydro-          chlorid    übergeführt werden kann. Dieses  kristallisiert aus Aceton in farblosen Kri  stallen vom F. 204-206 .

   Es ist leicht löslich    in     'Vasser.    Hydriert man dieses ungesättigte  Amin, so erhält man das     N-(y,y-Diphenyl-          propyl)-piperidin    der Formel  
EMI0002.0018     




  Process for the preparation of N- (r, r-diphenyl-allyl) -piperidine. The present invention relates to a process for the preparation of N- (y, y-diphenyl-allyl) -piperidine, which is characterized in that a fl-piperidino-propionic acid ester is reacted with a phenylmagnesium halide and from the so obtained y-piperidino-a, a-diphenyl-propanol- (a) water is eliminated.

      The new compound is an oil which is easily soluble in petroleum ether and which forms a hydrochloride of F. 204-206. It should be used as a remedy and for the production of medicinal products.

           Example: To a phenylmagnesium bromide solution of 157 parts by weight of bromobenzene and 24 parts by weight of magnesium in 300 cm3 of ether, 72 parts by weight of p-piperidino-propionic acid n-butyl ester, gp "137-138 of the formula
EMI0001.0020
         allowed to drip. Self-heating occurs, which keeps the ethereal solution in you. When the addition is complete, the mixture is refluxed for a further two hours.

   It is then poured into a mixture of 200 parts by volume of 37% hydrochloric acid and 800 parts by weight of ice, with stirring. The hydrochloride of y-piperidino-a, a-diphenyl-propanol- (a) of the formula which separates out in the process
EMI0001.0031
    is filtered off with suction, washed with ether, then with a little dilute hydrochloric acid, then again with ether and dried over sodium hydroxide in a vacuum desiclator.



  The product is a colorless crystal powder from F. 216 with decomposition, quite little soluble in cold water, more easily soluble in hot water, recrystallizable from alcohol. The base is a colorless, crystalline powder with a melting point of 119-120.



  In order to split off water, the base is expediently dissolved in three times the amount of 85% phosphoric acid and heated to 180-140 for 1 hour. Precipitation with sodium hydroxide gives the oily N- (y, y-diphenylallyl) piperidine of the formula
EMI0002.0012
    which can be absorbed in ether, separated and converted into hydrochloride using alcoholic hydrochloric acid. This crystallizes from acetone in colorless crystals from F. 204-206.

   It is easily soluble in 'Vasser. If this unsaturated amine is hydrogenated, the N- (y, y-diphenylpropyl) piperidine of the formula is obtained
EMI0002.0018

Claims (1)

PATEN'TANSPRUCU: Verfahren zur Herstellung von N-(y,y- Diphenyl-allyl)-piperidin, dadurch gekenn zeichnet, dass man einen ss-Piperidino-propion- säureester mit einem Phenylmagnesiumhalo- genid umsetzt und aus dem so erhaltenen <I>y -</I> Piperidino - a,a - diphenyl - propanol <I>- (a)</I> Wasser abspaltet. Die neue Verbindung ist ein in Petrol- äther leicht lösliches 01, das ein Hydrochlorid vom F. 204-206 bildet. PATEN'TANSPRUCU: Process for the production of N- (y, y-diphenyl-allyl) -piperidine, characterized in that an β-piperidino-propionic acid ester is reacted with a phenylmagnesium halide and the resulting <I> y - </I> Piperidino - a, a - diphenyl - propanol <I> - (a) </I> splits off water. The new compound is an oil which is easily soluble in petroleum ether and which forms a hydrochloride of F. 204-206. Sie soll als Heil mittel sowie für die Herstellung von Heil mitteln verwendet werden. It should be used as a remedy and for the production of medicinal products.
CH240363D 1941-05-24 1942-04-18 Process for the preparation of N- (y, y-diphenyl-allyl) -piperidine. CH240363A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE240363X 1941-05-24
DE234785X 1941-05-24

Publications (1)

Publication Number Publication Date
CH240363A true CH240363A (en) 1945-12-15

Family

ID=32870126

Family Applications (2)

Application Number Title Priority Date Filing Date
CH234785D CH234785A (en) 1941-05-24 1942-04-18 Process for the preparation of N- (y, y-diphenyl-allyl) -N, N-diethylamine.
CH240363D CH240363A (en) 1941-05-24 1942-04-18 Process for the preparation of N- (y, y-diphenyl-allyl) -piperidine.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH234785D CH234785A (en) 1941-05-24 1942-04-18 Process for the preparation of N- (y, y-diphenyl-allyl) -N, N-diethylamine.

Country Status (1)

Country Link
CH (2) CH234785A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2599364A (en) * 1949-01-26 1952-06-03 Hoffmann La Roche 1-alkyl-3-benzohydryl piperidines
US2665278A (en) * 1951-05-09 1954-01-05 Merck & Co Inc Gamma-hydroxy quaternary ammonium compounds
US2725399A (en) * 1949-11-03 1955-11-29 American Cyanamid Co Tertiary dialkylamino propanols

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2723269A (en) * 1949-11-03 1955-11-08 American Cyanamid Co Piperidino tertiary amino alcohols
US2716121A (en) * 1949-11-03 1955-08-23 American Cyanamid Co Basic tertiary piperidino alcohols

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2599364A (en) * 1949-01-26 1952-06-03 Hoffmann La Roche 1-alkyl-3-benzohydryl piperidines
US2725399A (en) * 1949-11-03 1955-11-29 American Cyanamid Co Tertiary dialkylamino propanols
US2665278A (en) * 1951-05-09 1954-01-05 Merck & Co Inc Gamma-hydroxy quaternary ammonium compounds

Also Published As

Publication number Publication date
CH234785A (en) 1944-10-31

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