DE744756C - Process for the preparation of 6-isoamylamino-2-methylheptane - Google Patents
Process for the preparation of 6-isoamylamino-2-methylheptaneInfo
- Publication number
- DE744756C DE744756C DEK163372D DEK0163372D DE744756C DE 744756 C DE744756 C DE 744756C DE K163372 D DEK163372 D DE K163372D DE K0163372 D DEK0163372 D DE K0163372D DE 744756 C DE744756 C DE 744756C
- Authority
- DE
- Germany
- Prior art keywords
- methylheptane
- amino
- isoamylamino
- methylhepten
- preparation
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 6
- RRWTWWBIHKIYTH-UHFFFAOYSA-N octamylamine Chemical compound CC(C)CCCC(C)NCCC(C)C RRWTWWBIHKIYTH-UHFFFAOYSA-N 0.000 title claims description 6
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 6
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- QNIVIMYXGGFTAK-UHFFFAOYSA-N octodrine Chemical compound CC(C)CCCC(C)N QNIVIMYXGGFTAK-UHFFFAOYSA-N 0.000 claims description 5
- -1 isoamyl halide Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 6-Isoamylamino-2-methylheptan Es ist bekannt, N-Monoalkyl- bzw. -aralkylsubstitutionsprodukte des 6-Amino-2-methylheptens-(2) in der Weise herzustellen, daß man 2-Methylhepten-(2)-on-(6) mit primären Alkyl-bzw. Aralkylaminen kondensiert und der gleichzeitigen oder nachträglichen Reduktion unterwirft oder daß man 6-Amino-2-methylhepten-(2) in üblicher Weise alkyliert bzw. aralkyliert (österr. Patentschriften 134 561, 135 705). Die so erhältlichen Verbindungen weisen krampflösende Wirkungen ähnlich denen des Papaverins auf.Process for the production of 6-isoamylamino-2-methylheptane It is known to produce N-monoalkyl or -aralkyl substitution products of 6-amino-2-methylheptens- (2) in such a way that 2-methylheptene- (2) - on- (6) with primary alkyl or. Aralkylamines condensed and subjected to simultaneous or subsequent reduction or that 6-amino-2-methylhepten- (2) is alkylated or aralkylated in the usual way (Austrian patents 134 561, 135 705). The compounds obtainable in this way have antispasmodic effects similar to those of papaverine.
Es wurde nun gefunden, daß man in analoger Weise zu einem ähnlich gebauten gesättigten Amin, dem .6-Isoamylamino-2-methylheptan gelangen kann, das den Vorzug einer wesentlich stärkeren Wirkung auf Krampfzustände besitzt als die oben angeführten bekannten krampflösenden Mittel. Weitere Vorzüge dieses neuen Amins sind seine analgetische Wirkung und die geringe zentralerregende Wirkung, wodurch unerwünschte Nebenwirkungen vermieden werden. Hinzu kommt schließlich noch, daß das neue Amin eine hervorragende Beständigkeit besitzt. Die besonders hohe krampflösende Wirkung der gesättigten Verbindung ist insofern überraschend, als gerade ungesättigte Verbindungen in der Regel stärker wirken als gesättigte. Zwecks Herstellung des neuen Amins kann man derart verfahren, daß man 2-Methylheptanon-(6) bzw. 2-Methylhepten-(2)-on-(6) mit Isoamylamin kondensiert und das Kondensationsprodukt, zweckmäßig mit naszierendem Wasserstoff, reduziert. Die beiden Reaktionen können auch in einem Arbeitsgang durchgeführt werden.It has now been found that one is similar in an analogous manner to one built saturated amine, the .6-Isoamylamino-2-methylheptane, the has the merit of a much stronger effect on convulsive states than that known antispasmodic agents listed above. Other benefits of this new amine are its analgesic effect and the low central stimulating effect, whereby unwanted side effects are avoided. Finally, there is also that the new amine has excellent stability. The particularly high antispasmodic The effect of the saturated compound is surprising in that it is precisely unsaturated Compounds usually act stronger than saturated ones. For the purpose of The new amine can be prepared in such a way that 2-methylheptanone- (6) or 2-methylhepten- (2) -one- (6) condensed with isoamylamine and the condensation product, expediently with nascent hydrogen, reduced. The two reactions can can also be carried out in one operation.
Nach einer Ausführungsform des erfindungsgemäßen Verfahrens kann man auch 6 Amino-2-methy lheptan bzw. 6-Amino-2-methy lhepten-(2) mit Isovaleraldehyd bei gleichzeitiger oder anschließender Reduktion kondensieren. Schließlich kann man auch auf 6-Amino-2-metliylheptan bzw. 6-Amino-2-methylhepten-(2) ein Isoamylhalogenid einwirken lassen und die im zweiten Falle entstehende ungesättigte Verbindung anschließend hydrieren.According to one embodiment of the process according to the invention, one can also 6 amino-2-methylheptane or 6-amino-2-methylhepten- (2) with isovaleraldehyde condense with simultaneous or subsequent reduction. Finally can one also uses 6-amino-2-methylheptane or 6-amino-2-methylhepten- (2) an isoamyl halide let act and then the resulting unsaturated compound in the second case hydrogenate.
Die überlegene spasmolytische Wirkung des so erhältlichen 6-Isoamylamino-2-methylheptans gegenüber dem 6-Methylamino-2-methylhepten-(2) geht aus folgenden pharmakologischen Daten hervor: i. Beim Vergleich der Wirkung auf den isolierten Kaninchendarm nach R. Magnus verhalten sich dieWirkungsstärken wie io : i.The superior spasmolytic effect of the 6-isoamylamino-2-methylheptane obtainable in this way compared to the 6-methylamino-2-methylhepten- (2) is based on the following pharmacological Data emerges: i. When comparing the effect on the isolated rabbit intestine after R. Magnus, the efficiencies behave like io: i.
z. Beim Vergleich der Stärken der Einwirkungen auf den isolierten Kaninchendarm nach künstlich erzeugtem Spasmus durch Bariumchlorid ergibt sich für die beiden Vergleichssubstanzen ebenfalls das Verhältnis 10 : i.z. When comparing the strengths of the effects on the isolated Rabbit intestine after artificially produced spasm by barium chloride results for the two comparison substances also have the ratio 10: i.
3. Bei der Prüfung am isolierten Meerschweinchendarm, der durch Acetvlcholin kontrahiert worden war, verhalten sich die Wirkungsstärken wie 10-30 : 1. Beispiel i 128g 2-Methylheptanon-(6) werden mit einer Lösung von 959 Isoamylamin in 6oo cm3 Alkohol und ioo cm3 Wasser versetzt und nach Zugabe von ioo g aktiviertem Aluminium i bis 2 Tage unter Rückfluß erhitzt. Nach beendigter Reaktion wird mit Salzsäure neutralisiert, und nichtbasische Anteile sowie der Alkohol werden mit Wasserdampf abdestilliert. Die wäßrige Lösung wird nun alkalisch gemacht, das sich abscheidende Öl in Äther aufgenommen und die Ätherlösung über Pottasche getrocknet. Nach dem Verdampfen des Äthers geht das 6-Isoamylamino-2-methylheptan unter einem Druck von 7 mm bei ioo bis ioi° über. Ausbeute: 82% d. Th.3. When tested on the isolated guinea pig ileum, which had been contracted by Acetvlcholin, the potencies behave as 10-30: Example 1 128g 2-i are Methylheptanon- (6) with a solution of isoamylamine in 959 cm3 6oo alcohol and ioo cm3 of water are added and, after adding 100 g of activated aluminum, the mixture is refluxed for 1 to 2 days. After the reaction has ended, it is neutralized with hydrochloric acid, and non-basic components and the alcohol are distilled off with steam. The aqueous solution is now made alkaline, the oil which separates out is taken up in ether and the ether solution is dried over potash. After evaporation of the ether, the 6-isoamylamino-2-methylheptane passes under a pressure of 7 mm at 100 to 10 °. Yield: 82% of theory Th.
Es stellt eine stark basische Flüssigkeit mit schwach aromatischem Geruch dar, die in Wasser unlöslich, in Säuren und organischen Lösungsmitteln leicht löslich ist.It represents a strongly basic liquid with weakly aromatic Odor that is insoluble in water, easily in acids and organic solvents is soluble.
Das Hydrochlorid der Base kristallisiert in glänzenden wachsartigen Blättchen vom F=i2i°; es ist wenig löslich in Wasser, licht löslich in organischen Lösungsmitteln, insbesondere in Äther.The hydrochloride of the base crystallizes in glossy waxy Leaflets from F = 12 °; it is sparingly soluble in water, lightly soluble in organic Solvents, especially in ether.
Beispiel e 129 g 6-Amino-2-methylheptan werden mit einer Lösung von 86g Isovaleraldehyd in 5oo cm3 Alkohol und Zoo cm3 Wasser versetzt und unter Zugabe von ioo g aktiviertem Aluminium i bis 2 Tage am Rückflußkühler erwärmt. Nach Beendigung der Reaktion wird mit verdünnter Mineralsäure bis zur Neutralisation versetzt und darauf nach Beispiel i weiter aufgearbeitet. Beispiel 3 6-1e5 g 6-Amino-2-methylheptan werden mit 30,2 g Isoamylbromid unter Rückfluß erhitzt. Nach beendigter Reaktion wird noch etwa 6 Stunden weiter erwärmt. Nach dem Erkalten und Ansäuern mit Salzsäure werden gcringe Mengen nichtbasischer Anteile mit Wasserdampf abdestilliert. Durch Zusatz von Alkalilauge wird ein Öl abgeschieden, aus dem durch fraktionierte Destillation unter einem Druck von 18 mm bei i 15 bis i 18° das 6-Isoamylamino-2-methylheptan als farblose Flüssigkeit in einer Ausbeute von 96% d. Th. gewonnen wird.EXAMPLE e 129 g of 6-amino-2-methylheptane are mixed with a solution of 86 g of isovaleraldehyde in 500 cm3 of alcohol and zoo cm3 of water and heated in a reflux condenser for 1 to 2 days with the addition of 100 g of activated aluminum. After the reaction has ended, dilute mineral acid is added until neutralization and then worked up further according to Example i. Example 3 6-1e5 g of 6-amino-2-methylheptane are refluxed with 30.2 g of isoamyl bromide. After the reaction has ended, heating is continued for about 6 hours. After cooling and acidification with hydrochloric acid, small amounts of non-basic components are distilled off with steam. An oil is separated out by adding alkali, from which the 6-isoamylamino-2-methylheptane is obtained as a colorless liquid in a yield of 96% of theory by fractional distillation under a pressure of 18 mm at 15 to 18 °. Th. Is won.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK163372D DE744756C (en) | 1942-01-14 | 1942-01-14 | Process for the preparation of 6-isoamylamino-2-methylheptane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK163372D DE744756C (en) | 1942-01-14 | 1942-01-14 | Process for the preparation of 6-isoamylamino-2-methylheptane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE744756C true DE744756C (en) | 1951-01-29 |
Family
ID=7254477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK163372D Expired DE744756C (en) | 1942-01-14 | 1942-01-14 | Process for the preparation of 6-isoamylamino-2-methylheptane |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE744756C (en) |
-
1942
- 1942-01-14 DE DEK163372D patent/DE744756C/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
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