CH314914A - Process for the preparation of novel amino-10-alkyl-phenothiazines - Google Patents
Process for the preparation of novel amino-10-alkyl-phenothiazinesInfo
- Publication number
- CH314914A CH314914A CH314914DA CH314914A CH 314914 A CH314914 A CH 314914A CH 314914D A CH314914D A CH 314914DA CH 314914 A CH314914 A CH 314914A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- phenothiazines
- preparation
- amino
- phenothiazine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229950000688 phenothiazine Drugs 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
<B>Procédé de préparation de nouvelles</B> amino-alcoyl-10-phénothiazines La présente invention a pour objet un pro cédé de préparation de nouvelles amines dé rivées de la phénothiazine, les amino-alcoyl- 10-phénothiazines dans lesquelles le substituant amino-alcoyle est de la forme CnH2,,NH2, où<I>n</I> est un nombre entier égal à 2 ou 3.
Ces nou velles amino-alcoyl-10-phénothiazines peuvent être représentés par la formule générale
EMI0001.0008
dans laquelle X représente un atome d'hydro gène, un atome d'halogène ou un reste alcoyle inférieur situé plus particulièrement en position 1 ou 3 du noyau de la phénothiazine (numéro tation Beilstein).
Le procédé selon l'invention est caracté risé en ce qu'on fait réagir de l'ammoniac sur l'halogénoalcoyl-10-phénothiazine correspon dant à l'amine à obtenir.
Ces amino-alcoyl-10-phénothiazines consti tuent des produits intermédiaires importants pour la préparation de corps doués d'actions pharmacodynamiques intéressantes.
Les exemples suivants montrent comment le procédé selon l'invention peut être mis en pra tique. Les points de fusion indiqués ont été déter minés au banc Kofler. <I>Exemple 1</I> On prépare la chloro-3-(chloro-3'-propyl)- 10-phénothiazine par analogie avec la méthode décrite par Gilman et Shirley, Am. Soc. 66, 890 (1944).
On chauffe en autoclave, 14 heures à 100 , une solution de 10 g de chloro-3-(chloro-3'- propyl)-10-phénothiazine brute dans 25 cm3 d'alcool éthylique et 14 g de gaz ammoniac.
Après concentration, on traite avec 120 cm3 d'acide chlorhydrique à 10 % à 500, en ex trayant l'insoluble avec 50 cm-' de benzène.
Par addition de 20 cm3 de soude d=1,33 à la solution chlorhydrique et extraction avec 120 cm3 d'éther, on isole la base brute.
Le maléate acide de la chloro-3-(amino-3'- propyl)-10-phénothiazine fond à 191-192,1 C. <I>Exemple 2:</I> On chauffe en autoclave, 16 heures à 1800, 13 g de (chloro-2'éthyl)-10-phénothiazine (pré parée selon Gilman et Shirley, loc. cit.) dans 30 cm3 d'alcool éthylique avec 23 g d'ammo niac. On traite le produit de la réaction comme dans l'exemple 1 et sépare l'(amino-2'-éthyl)- 10-phénothiazine sous forme de chlorhydrate, qui fond à 270-271 C. .
Le maléate acide d'(amino-2'-éthyl)-10- phénothiazine fond à 181o C.
<B> Process for the preparation of new </B> amino-alkyl-10-phenothiazines The present invention relates to a process for the preparation of novel amines derived from phenothiazine, the amino-alkyl-10-phenothiazines in which the amino-alkyl substituent is of the form CnH2,, NH2, where <I> n </I> is an integer equal to 2 or 3.
These new amino-10-alkyl-phenothiazines can be represented by the general formula
EMI0001.0008
in which X represents a hydrogen atom, a halogen atom or a lower alkyl residue located more particularly in position 1 or 3 of the nucleus of the phenothiazine (Beilstein number).
The process according to the invention is characterized in that ammonia is reacted with the haloalkyl-10-phenothiazine corresponding to the amine to be obtained.
These amino-alkyl-10-phenothiazines are important intermediates for the preparation of bodies endowed with valuable pharmacodynamic actions.
The following examples show how the process according to the invention can be put into practice. The indicated melting points were determined on the Kofler bench. <I> Example 1 </I> Chloro-3- (chloro-3'-propyl) - 10-phenothiazine is prepared by analogy with the method described by Gilman and Shirley, Am. Soc. 66, 890 (1944).
A solution of 10 g of crude chloro-3- (chloro-3'-propyl) -10-phenothiazine in 25 cm3 of ethyl alcohol and 14 g of ammonia gas is heated in an autoclave for 14 hours at 100.
After concentration, it is treated with 120 cm3 of 10% hydrochloric acid at 500, while extracting the insoluble material with 50 cm 3 of benzene.
By adding 20 cm3 of sodium hydroxide d = 1.33 to the hydrochloric acid solution and extraction with 120 cm3 of ether, the crude base is isolated.
The chloro-3- (amino-3'-propyl) -10-phenothiazine acid maleate melts at 191-192.1 C. <I> Example 2: </I> The mixture is heated in an autoclave for 16 hours at 1800, 13 g of (chloro-2′ethyl) -10-phenothiazine (prepared according to Gilman and Shirley, loc. Cit.) In 30 cm3 of ethyl alcohol with 23 g of ammonia. The reaction product is worked up as in Example 1 and the (amino-2'-ethyl) -10-phenothiazine is separated off as the hydrochloride, which melts at 270-271 C.
(Amino-2'-ethyl) -10-phenothiazine acid maleate melts at 181o C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH314914T | 1953-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314914A true CH314914A (en) | 1956-07-15 |
Family
ID=4495781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314914D CH314914A (en) | 1953-05-21 | 1953-05-21 | Process for the preparation of novel amino-10-alkyl-phenothiazines |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314914A (en) |
-
1953
- 1953-05-21 CH CH314914D patent/CH314914A/en unknown
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