CH127779A - Process for the preparation of a piperide derivative substituted in position B and Y. - Google Patents

Process for the preparation of a piperide derivative substituted in position B and Y.

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Publication number
CH127779A
CH127779A CH127779DA CH127779A CH 127779 A CH127779 A CH 127779A CH 127779D A CH127779D A CH 127779DA CH 127779 A CH127779 A CH 127779A
Authority
CH
Switzerland
Prior art keywords
preparation
derivative substituted
piperide
piperidine
hydrochloride
Prior art date
Application number
Other languages
French (fr)
Inventor
De Montmollin Marcel Dr Prof
Original Assignee
De Montmollin Marcel Dr Prof
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 De Montmollin Marcel Dr Prof filed Critical De Montmollin Marcel Dr Prof
Publication of CH127779A publication Critical patent/CH127779A/en

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Description

  

  Procédé de préparation d'un dérivé     pipéridique    substitué en position     (3    et     r.       La présente invention concerne un pro  cédé pour la préparation d'un dérivé     pipéri-          dique    substitué en position     fi    et y, selon le  quel on traite le     dinitrile    correspondant à  la formule  
EMI0001.0008     
    avec des agents réducteurs et cyclise la dia  mine ainsi obtenue par distillation sèche de  son chlorhydrate.  



  La cyclisation peut être représentée par  le schéma suivant:  
EMI0001.0009     
    La     P-éthyle-y-méthyle-pipéridine    ainsi  obtenue forme un liquide incolore, soluble    dans l'eau, l'alcool et l'éther, dont l'odeur  ressemble à celle de la.     pipéridine.    Son     chlor-          hydrate,    hygroscopique, est     infusible    à  une température inférieure à 250   C. Elle  constitue une matière première de grande  valeur pour la synthèse de     certains    alca  loïdes, par exemple de la quinine.  



  <I>Exemple:</I>  On ajoute à 15     parties    en poids de 2  méthyle-pentanedinitrile-1.3 (point d'ébul  lition sous 12 mm de mercure 189 à     192'),     dissous dans 500 parties     .en    volume d'alcool  absolu, 80 parties en poids de sodium et  on chauffe le mélange au reflux. On distille  ensuite l'alcool et on soumet le résidu con  tenant la     2-éthyle-3-méthyle-pentaméthy-          lène-diamine    à la distillation à la vapeur  d'eau. L'amine contenue dans la     solution     aqueuse est extraite à l'éther, l'éther est  séché et évaporé et le résidu est distillé  sous pression réduite.

   La     2-éthyle-3-méthyle-          pentaméthylène-diamine    ainsi obtenue forme  un liquide soluble dans l'eau, l'alcool et  l'éther, possédant un point -d'ébullition de  100 à 103   sous 12 mm de mercure.      4 parties en poids de cette diamine, dis  soute dans 60 parties en volume d'éther ab  solu, sont saturées d'acide chlorhydrique ri  goureusement sec en refroidissant; des       cristaux    blancs se séparent immédiatement.  L'éther et l'acide en excès sont chassés et le  résidu est chauffé fortement à feu nu. Le       chlorhydrate    de la diamine fond tout d'a  bord, entre en ébullition et un liquide qui  est la     f-éthyle-y-méthyle-pipéridine    se con  dense dans le récipient.  



  Le     2-méthyle-pentanedinitrile-1.3,    ser  vant de matière initiale, peut être obtenu à  partir du     2-méthyle-pentanediol-1    . 3 par son       dibromure    correspondant. Le     dibromure    est  un liquide bouillant sous 12 mm de mercure  à 79-83  : il est transformé en     dinitrile    de  manière connue par traitement au cyanure  de     potassium    en solution alcoolique.



  Process for the preparation of a piperide derivative substituted in position (3 and r. The present invention relates to a process for the preparation of a piperide derivative substituted in position fi and y, according to which the dinitrile corresponding to the position is treated. formula
EMI0001.0008
    with reducing agents and cyclizes the diameter thus obtained by dry distillation of its hydrochloride.



  Cyclization can be represented by the following diagram:
EMI0001.0009
    The P-ethyl-y-methyl-piperidine thus obtained forms a colorless liquid, soluble in water, alcohol and ether, the odor of which resembles that of. piperidine. Its hydrochloride, hygroscopic, is infusible at a temperature below 250 C. It constitutes a raw material of great value for the synthesis of certain alkaloids, for example quinine.



  <I> Example: </I> Is added to 15 parts by weight of 2 methyl-pentanedinitrile-1.3 (boiling point under 12 mm of mercury 189 to 192 '), dissolved in 500 parts by volume of alcohol absolute, 80 parts by weight of sodium and the mixture is heated to reflux. The alcohol is then distilled off and the residue containing 2-ethyl-3-methyl-pentamethylenediamine is subjected to steam distillation. The amine contained in the aqueous solution is extracted with ether, the ether is dried and evaporated and the residue is distilled off under reduced pressure.

   The 2-ethyl-3-methyl-pentamethylene-diamine thus obtained forms a liquid soluble in water, alcohol and ether, having a boiling point of 100 to 103 at 12 mm of mercury. 4 parts by weight of this diamine, dissolved in 60 parts by volume of dissolved ether, are saturated with hydrochloric acid, which is very dry on cooling; white crystals immediately separate. The ether and excess acid are driven off and the residue is heated strongly over open fire. The diamine hydrochloride immediately melts, boils, and a liquid which is β-ethyl-y-methyl-piperidine thickens in the container.



  2-Methyl-pentanedinitrile-1.3, used as the starting material, can be obtained from 2-methyl-pentanediol-1. 3 by its corresponding dibromide. Dibromide is a liquid boiling under 12 mm of mercury at 79-83: it is transformed into dinitrile in a known manner by treatment with potassium cyanide in an alcoholic solution.

Claims (1)

REVENDICATION Procédé de préparation d'un dérivé pi péridique substitué en position (1 et y, selon lequel on traite le dinitrile correspondant à la formule EMI0002.0012 avec des agents réducteurs et cyclise la dia mine ainsi obtenue par distillation sèche de son chlorhydrate. La P-éthyle-y-mathyle-pipéridine ainsi obtenue forme un liquide incolore, soluble dans l'eau, l'alcool et l'éther, dont l'odeur ressemble à celle de la pipéridine. Son chlor- hydrate, hygroscopique, est infusible à une température inférieure à 250 C. CLAIM Process for the preparation of a pi peridic derivative substituted in position (1 and y, according to which the dinitrile corresponding to the formula is treated. EMI0002.0012 with reducing agents and cyclizes the diameter thus obtained by dry distillation of its hydrochloride. The P-ethyl-y-mathyl-piperidine thus obtained forms a colorless liquid, soluble in water, alcohol and ether, the odor of which resembles that of piperidine. Its hydrochloride, hygroscopic, is infusible at a temperature below 250 C. Elle cons titue une matière première de grande va leur pour la synthèse de certains alcaloïdes, par exemple de la quinine. It constitutes a raw material of great value for the synthesis of certain alkaloids, for example quinine.
CH127779D 1927-05-09 1927-05-09 Process for the preparation of a piperide derivative substituted in position B and Y. CH127779A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH127779T 1927-05-09

Publications (1)

Publication Number Publication Date
CH127779A true CH127779A (en) 1928-10-01

Family

ID=4386297

Family Applications (1)

Application Number Title Priority Date Filing Date
CH127779D CH127779A (en) 1927-05-09 1927-05-09 Process for the preparation of a piperide derivative substituted in position B and Y.

Country Status (1)

Country Link
CH (1) CH127779A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2657208A (en) * 1951-12-03 1953-10-27 Univ Michigan Process for preparing 1-methyl-4-phenyl-4-cyanopiperidine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2657208A (en) * 1951-12-03 1953-10-27 Univ Michigan Process for preparing 1-methyl-4-phenyl-4-cyanopiperidine

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