DE1079067B - Process for the preparation of 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane and its salts - Google Patents

Process for the preparation of 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane and its salts

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Publication number
DE1079067B
DE1079067B DEN13714A DEN0013714A DE1079067B DE 1079067 B DE1079067 B DE 1079067B DE N13714 A DEN13714 A DE N13714A DE N0013714 A DEN0013714 A DE N0013714A DE 1079067 B DE1079067 B DE 1079067B
Authority
DE
Germany
Prior art keywords
ethylaminopentane
methylenedioxyphenyl
salts
preparation
hydrogenated
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.)
Pending
Application number
DEN13714A
Other languages
German (de)
Inventor
Dr Rer Nat Richard Gutbrod
Dr Viktor Wolf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nordmark Werke GmbH
Original Assignee
Nordmark Werke GmbH
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 Nordmark Werke GmbH filed Critical Nordmark Werke GmbH
Priority to DEN13714A priority Critical patent/DE1079067B/en
Publication of DE1079067B publication Critical patent/DE1079067B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von 1-(3',4'-Methylendioxyphenyl)-3-äthylaminopentan und seinen Salzen Es sind eine Reihe von substituierten l-Phenyl-3-aminopentanderivaten, z. B. die Alkoxyphenyl-3-alkylaminopentane, beschrieben worden, diepharmazeutisch verwertbare Eigenschaften besitzen. Process for the preparation of 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane and its salts There are a number of substituted l-phenyl-3-aminopentane derivatives, z. The alkoxyphenyl-3-alkylaminopentanes, which are pharmaceutical have usable properties.

Diese Substanzen werden durch Hydrierung mittels naszierenden Wasserstoffs oder katalytisch erregten Wasserstoffs aus den entsprechenden, in der Seitenkette gesättigten oder. ungesättigten 3-Ketoverbindungen hergestellt, wobei die Hydrierung in Gegenwart von Ammoniak oder den entsprechenden Aminen durchgeführt wird. Die bekannten Verbindungen sind nach den Angaben der Literatur sämtlich analgetisch wirksam. These substances are hydrogenated using nascent hydrogen or catalytically excited hydrogen from the corresponding, in the side chain saturated or. unsaturated 3-keto compounds produced, the hydrogenation is carried out in the presence of ammonia or the corresponding amines. the known compounds are all analgesic according to the information in the literature effective.

Es wurde nun gefunden, daß das noch unbekannte 1- (3',4'-Methylendioxyphenyl) -3-äthylaminopentan der Formel und seine Salze, vorzugsweise sein Hydrochlorid, im Gegensatz zu den ähnlich gebauten, schon bekannten Substanzen überraschenderweise keine analgetische Wirkung, wohl aber eine noch nicht bekannte Kreislaufwirksamkeit im Sinne einer zentralen, coronar-und periphergefäßerweiternden Wirkung besitzen.It has now been found that the as yet unknown 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane of the formula and its salts, preferably its hydrochloride, in contrast to the similarly built, already known substances, surprisingly have no analgesic effect, but have as yet unknown circulatory activity in the sense of a central, coronary and peripheral vasodilating effect.

Weiterhin haben die neuen Verbindungen eine broncholytische und atemanaleptische Wirkung und eine für solche Substanzen noch nicht beschriebene zentralstimulierende Wirkung.Furthermore, the new compounds are broncholytic and breath-maleptic Effect and a centrally stimulating effect not yet described for such substances Effect.

Das 1- (3',4' - Methylendioxyphenyl) - 3- äthylaminopentan wird erfindungsgemäß hergestellt, indem man 3,4-Methylendioxystyryl-äthylketon in an sich bekannter Weise in Gegenwart von überschüssigem Ethylamin in methanolischer Lösung mit Hilfe von Raneynickel hydriert. Man verwendet dabei Temperaturen von etwa 40 bis 1200 C und Wasserstoffdrücke von etwa 80 bis 120 Atmosphären. Das 1- (3',4' - Methylendioxyphenyl) - 3 - äthylaminopentan wird gegebenenfalls in an sich bekannter Weise mit Säuren in seine Salze übergeführt. The 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane is according to the invention prepared by adding 3,4-methylenedioxystyryl ethyl ketone in a manner known per se in the presence of excess ethylamine in methanolic solution with the aid of Raney nickel hydrogenated. Temperatures of about 40 to 1200 C and are used Hydrogen pressures of about 80 to 120 atmospheres. The 1- (3 ', 4' - methylenedioxyphenyl) - 3 - Ethylaminopentane is optionally treated with acids in a manner known per se converted into its salts.

Beispiel In einem 4,5-l-Autoklav wird eine Mischung aus 250 g 3,4- Methylendioxystyryl - äthylketon (K. Ivamoto, Bulletin of the Chemical Society of Japan, 2, 1953), 300 g wasserfreiem Äthylamin in 2,51 gekühltem Methanol und 3 Spatelspitzen Raneynickel 9 Stunden bei 80 atü und 800 C hydriert. Nach Öffnen des Autoklavs wird der Inhalt in eine Flasche gesaugt und filtriert. Man dampft das Lösungsmittel auf dem Wasserbad ab und entfernt die letzten Reste Methanol im Vakuum. Example A mixture of 250 g of 3.4- Methylenedioxystyryl ethyl ketone (K. Ivamoto, Bulletin of the Chemical Society of Japan, 2, 1953), 300 g of anhydrous ethylamine in 2.5 liters of chilled methanol and 3 spatula tips Raney nickel hydrogenated at 80 atmospheres and 800 ° C. for 9 hours. After opening the autoclave the contents sucked into a bottle and filtered. The solvent is evaporated the water bath and removes the last residues of methanol in vacuo.

Den Rückstand destilliert man bei 1 mm und 130 bis 1400 C und erhält 225 g eines farblosen Öles. The residue is distilled at 1 mm and 130 to 1400 ° C. and obtained 225 g of a colorless oil.

Man nimmt das Öl in 600 ccm getrockneten Äther auf und leitet trockenes Salzsäuregas bis zur schwach sauren Reaktion ein. Dann läßt man einige Zeit stehen, bis das Hydrochlorid fest wird. Man kristallisiert zweimal aus 1 1 Essigester um. The oil is taken up in 600 cc of dried ether and dried Hydrochloric acid gas until the reaction is weakly acidic. Then you let stand for a while until the hydrochloride solidifies. It is recrystallized twice from 1 l of ethyl acetate.

Ausbeute: 100 g=300/o der Theorie, F. 132 bis 1330 C. Yield: 100 g = 300 / o of theory, mp 132 to 1330 C.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von 1-(3',4'-Methylendioxyphenyl) -3-äthylaminopentan und seinen Salzen, dadurch gekennzeichnet, daß man 3,4-Methylendioxystyryl-äthylketon in an sich bekannter Weise in Gegenwart von überschüssigem Athylamin mit Hilfe von Raneynickel hydriert und gegebenenfalls die erhaltene Base mit Säuren behandelt. ~~~~~~~ In Betracht gezogene Druckschriften: USA.-Patentschrift Nr. 2495 404. PATENT CLAIM Process for the production of 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane and its salts, characterized in that 3,4-methylenedioxystyryl ethyl ketone in a manner known per se in the presence of excess ethylamine with the aid of Raney nickel is hydrogenated and, if appropriate, the base obtained is treated with acids. ~~~~~~~ References considered: USA.Patent No. 2495404.
DEN13714A 1957-05-29 1957-05-29 Process for the preparation of 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane and its salts Pending DE1079067B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEN13714A DE1079067B (en) 1957-05-29 1957-05-29 Process for the preparation of 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane and its salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEN13714A DE1079067B (en) 1957-05-29 1957-05-29 Process for the preparation of 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane and its salts

Publications (1)

Publication Number Publication Date
DE1079067B true DE1079067B (en) 1960-04-07

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEN13714A Pending DE1079067B (en) 1957-05-29 1957-05-29 Process for the preparation of 1- (3 ', 4'-methylenedioxyphenyl) -3-ethylaminopentane and its salts

Country Status (1)

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DE (1) DE1079067B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339878A2 (en) * 1988-04-25 1989-11-02 Eli Lilly And Company Propanamine derivatives

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2495404A (en) * 1945-05-08 1950-01-24 Geigy Ag J R Alkoxyphenylalkyl-alkyl amines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2495404A (en) * 1945-05-08 1950-01-24 Geigy Ag J R Alkoxyphenylalkyl-alkyl amines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339878A2 (en) * 1988-04-25 1989-11-02 Eli Lilly And Company Propanamine derivatives
EP0339878A3 (en) * 1988-04-25 1990-12-05 Eli Lilly And Company Propanamine derivatives

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