CH308496A - Process for the preparation of a novel derivative of phenothiazine. - Google Patents

Process for the preparation of a novel derivative of phenothiazine.

Info

Publication number
CH308496A
CH308496A CH308496DA CH308496A CH 308496 A CH308496 A CH 308496A CH 308496D A CH308496D A CH 308496DA CH 308496 A CH308496 A CH 308496A
Authority
CH
Switzerland
Prior art keywords
phenothiazine
preparation
methyl
pyrrolidino
novel derivative
Prior art date
Application number
Other languages
French (fr)
Inventor
Rhone-Poulenc Societ Chimiques
Original Assignee
Rhone Poulenc Chemicals
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 Rhone Poulenc Chemicals filed Critical Rhone Poulenc Chemicals
Publication of CH308496A publication Critical patent/CH308496A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Description

  

  <B>Procédé de préparation d'un nouveau dérivé de la</B>     phénothiazine.       On a décrit, au brevet principal N  304883,  la préparation de     nouveaux    dérivés de la       phénothiazine    par condensation d'une     phéno-          thiazine,    substituée en position 1 (ou 3) par  un groupe alcoyle ou     alcoxy    inférieur, avec  un     diméthylaminohalogénopropane    ou un       pyrrolidinohalogénopropane,    ces produits pou  vant être utilisés en médecine humaine et  vétérinaire,

   et en particulier comme     pot.entia-          lisateurs    des anesthésiques généraux ou locaux  et des analgésiques.  



  Le brevet principal a. pour objet un pro  cédé de préparation de     (diméthylamino-3'-          propy    1-l.')     -10-méthyl-3-phénothiazine.     



  Le présent. brevet. a. pour objet. un procédé  de préparation d'un dérivé du même genre,  susceptible d'un même emploi, la     (pyrrolidino-          3'-propyl-1')-10-méthyl-3-phénothiazine,    carac  térisé en ce que l'on condense un     pyrrolidino-          3-halogéno-1-propane    avec la,     méthyl-3-phéno-          thiazine.     



  L'exemple suivant montre comment le pro  cédé peut être mis en     aeuvr    e.  



  On opère comme indiqué à. l'exemple du  brevet principal, en employant 15,9     g    de mé-         thyl-3-phénothiazine    préparée par condensa  tion du soufre sur la     méthyl-3-diphénylamine,     13,8     g    de     pyrrolidino-3-ehloro-1-propane    en  solution     xylénique    et 4,2 g     d'amidure    de so  dium à 80 %. On obtient 14,9 g de     (pyrrol-          idino-3'-propyl-l')        -10-méthyl    - 3 -     phénothiazine          (Ebo,is    = 207-212  C), dont     l'oxalate    fond à  175  C.



  <B> Process for the preparation of a novel derivative of </B> phenothiazine. The preparation of new phenothiazine derivatives by condensation of a phenothiazine, substituted in position 1 (or 3) with an alkyl or lower alkoxy group, with a dimethylaminohalopropane or a pyrrolidinohalopropane, has been described in main patent N 304883, these products can be used in human and veterinary medicine,

   and in particular as potentia-izers of general or local anesthetics and analgesics.



  The main patent a. for object a process for the preparation of (dimethylamino-3'-propy 1-l. ') -10-methyl-3-phenothiazine.



  The present. patent. at. for purpose. a process for the preparation of a derivative of the same kind, capable of the same use, (pyrrolidino-3'-propyl-1 ') - 10-methyl-3-phenothiazine, characterized in that one condenses a pyrrolidino-3-halo-1-propane with 1α, methyl-3-phenothiazine.



  The following example shows how the process can be implemented.



  We operate as indicated in. the example of the main patent, employing 15.9 g of methyl-3-phenothiazine prepared by condensing sulfur with methyl-3-diphenylamine, 13.8 g of pyrrolidino-3-ehloro-1-propane in xylene solution and 4.2 g of 80% sodium amide. 14.9 g of (pyrrol-idino-3'-propyl-1 ') -10-methyl-3-phenothiazine (Ebo, is = 207-212 C) are obtained, the oxalate of which melts at 175 C.

Claims (1)

REVENDICATION: Procédé de préparation de (pyrrolidino-3'- propyl-1')-10-méthyl-3-phénothiazine, caracté risé en ce que l'on condense un pyrrolidino-3- halogéno-1-propane avec la méthyl-3-phéno- thiazine. La substance obtenue a un Ebo.i5 de 207-212 C; son oxalate fond à 175 C. SOUS-REVENDICATIONS 1. Procédé selon la revendication, carac térisé en ce que l'on emploie le pyrrolidino-3- chloro-1-propane. 2. CLAIM: Process for the preparation of (pyrrolidino-3'-propyl-1 ') - 10-methyl-3-phenothiazine, characterized in that a pyrrolidino-3-halogeno-1-propane is condensed with methyl-3 -phenothiazine. The resulting substance has an Ebo.i5 of 207-212 C; its oxalate melts at 175 C. SUB-CLAIMS 1. A process according to claim, characterized in that pyrrolidino-3-chloro-1-propane is used. 2. Procédé selon la revendication, carac térisé en ce que la condensation est effectuée en présence d'un accepteur d'acide. Process according to claim, characterized in that the condensation is carried out in the presence of an acid acceptor.
CH308496D 1951-07-24 1952-05-12 Process for the preparation of a novel derivative of phenothiazine. CH308496A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR308496X 1951-07-24
CH304883T 1952-05-12

Publications (1)

Publication Number Publication Date
CH308496A true CH308496A (en) 1955-07-15

Family

ID=25734892

Family Applications (1)

Application Number Title Priority Date Filing Date
CH308496D CH308496A (en) 1951-07-24 1952-05-12 Process for the preparation of a novel derivative of phenothiazine.

Country Status (2)

Country Link
BE (1) BE540458A (en)
CH (1) CH308496A (en)

Also Published As

Publication number Publication date
BE540458A (en)

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