CH238285A - Process for preparing N-para-tolyl-N-benzyl-N'.N'-dimethyl-ethylenediamine. - Google Patents
Process for preparing N-para-tolyl-N-benzyl-N'.N'-dimethyl-ethylenediamine.Info
- Publication number
- CH238285A CH238285A CH238285DA CH238285A CH 238285 A CH238285 A CH 238285A CH 238285D A CH238285D A CH 238285DA CH 238285 A CH238285 A CH 238285A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- benzyl
- para
- dimethyl
- tolyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 6
- KEVOWRWHMCBERP-UHFFFAOYSA-N n-benzyl-4-methylaniline Chemical compound C1=CC(C)=CC=C1NCC1=CC=CC=C1 KEVOWRWHMCBERP-UHFFFAOYSA-N 0.000 claims description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- 229960001340 histamine Drugs 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000012512 characterization method Methods 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical group CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation de la N-para-tolyl-N-benzyl-N'. N'-diméthyl-éthylènediamine. La présente invention, dont l'auteur est M. Mosnier, a pour objet un procédé -de pré paration .de la N-para-tolyl-N-benzyl-N'. N'- diméthyl-éthylènediamine ,de formule:
EMI0001.0009
On a constaté que les sels de cette diamine possèdent des propriétés pharmaceutiques pré cieuses en ce sens qu'ils joignent à une toxi cité relativement faible et -à une tolérance satisfaisante une activité particulièrement élevée contre les phénomènes provoqués par l'action de l'histamine sur les organismes vi vants.
Le procédé objet da l'invention est carac térisé en ce que l'on condense de la N-benzyl- para-toluidine avec un diméthyl-aminoéthane substitué en P par un groupe condensable avec l'hydrogène du groupe amino de la N-benzyl- para-toluidine. On peut .donc condenser la N-benzyl-para- toluidine avec un fl halogénure, par exemple le chlorure ou le bromure,
du diméthyl- aminoéthane, ou même avec le diméthyl- aminoéthanol, dans # dernier cas avec l'aide. d'un agent dé condensation tel que P'O5 ou Zn Clz.
Voici, à titre d'exemple, comment le pro cédé de l'invention peut être exécuté: On chauffe à 140 pendant 10 h. 197 g -de N-benzyl-paratoluidine et 72 g -de chlor hydrate de @diméthylamino-p-chloréthane. La masse fondue est reprise par l'eau et les im puretés sont extraites par du benzène.
Par alcalinisation ultérieure jusqu'à virage rouge à la phénolphtaléïne, les bases sont mises en liberté et extraites au benzène. On distille le benzène puis, sous pression réduite à 3 mm, l a N - benzyl - N - paratolyl-N' . N'-diméthyl- éthylènediamine passant de 170 à 173 .
Le chlorhydrate -de cette base fond à 220 C.
Process for preparing N-para-tolyl-N-benzyl-N '. N'-Dimethyl-ethylenediamine. The present invention, of which the author is M. Mosnier, relates to a process -depre paration .de N-para-tolyl-N-benzyl-N '. N'-dimethyl-ethylenediamine, of the formula:
EMI0001.0009
It has been found that the salts of this diamine have valuable pharmaceutical properties in that they combine relatively low toxicity and satisfactory tolerance with a particularly high activity against the phenomena caused by the action of histamine. on living organisms.
The process which is the subject of the invention is characterized in that N-benzyl-para-toluidine is condensed with a dimethyl-aminoethane substituted at P by a group condensable with hydrogen of the amino group of N-benzyl - para-toluidine. The N-benzyl-para-toluidine can therefore be condensed with a halide, for example the chloride or the bromide,
dimethylaminoethane, or even with dimethylaminoethanol, in the latter case with help. a de-condensing agent such as P'O5 or Zn Clz.
Here is, by way of example, how the process of the invention can be carried out: Heat at 140 for 10 h. 197 g of N-benzyl-paratoluidine and 72 g of dimethylamino-p-chloroethane hydrochloride. The melt is taken up in water and the im purities are extracted with benzene.
By subsequent alkalization to a red turn with phenolphthalein, the bases are set free and extracted with benzene. The benzene is distilled off and then, under reduced pressure to 3 mm, the N - benzyl - N - paratolyl-N '. N'-dimethyl-ethylenediamine from 170 to 173.
The hydrochloride of this base melts at 220 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR238285X | 1941-05-24 | ||
| CH237502T | 1942-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH238285A true CH238285A (en) | 1945-06-30 |
Family
ID=25728259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH238285D CH238285A (en) | 1941-05-24 | 1942-02-25 | Process for preparing N-para-tolyl-N-benzyl-N'.N'-dimethyl-ethylenediamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH238285A (en) |
-
1942
- 1942-02-25 CH CH238285D patent/CH238285A/en unknown
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