DE2335079C3 - Aminoalkyl derivatives of 3,5-dimethylbenzoic acid and their salts and processes for their preparation - Google Patents

Aminoalkyl derivatives of 3,5-dimethylbenzoic acid and their salts and processes for their preparation

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Publication number
DE2335079C3
DE2335079C3 DE2335079A DE2335079A DE2335079C3 DE 2335079 C3 DE2335079 C3 DE 2335079C3 DE 2335079 A DE2335079 A DE 2335079A DE 2335079 A DE2335079 A DE 2335079A DE 2335079 C3 DE2335079 C3 DE 2335079C3
Authority
DE
Germany
Prior art keywords
dimethylbenzoic acid
salts
preparation
processes
aminoalkyl derivatives
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
Application number
DE2335079A
Other languages
German (de)
Other versions
DE2335079A1 (en
DE2335079B2 (en
Inventor
Jose Maria Castellano Berlanga
Miguel Fernandez Brana
Cristobal Martinez Roldan
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.)
Laboratories Made Sa Madrid
Original Assignee
Laboratories Made Sa Madrid
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
Priority claimed from ES411876A external-priority patent/ES411876A1/en
Application filed by Laboratories Made Sa Madrid filed Critical Laboratories Made Sa Madrid
Publication of DE2335079A1 publication Critical patent/DE2335079A1/en
Publication of DE2335079B2 publication Critical patent/DE2335079B2/en
Application granted granted Critical
Publication of DE2335079C3 publication Critical patent/DE2335079C3/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

Die Erfindung betrifft Aminoalkylderivate der 3,5-Dimethylbenzoesäure der allgemeinen FormelThe invention relates to aminoalkyl derivatives of 3,5-dimethylbenzoic acid the general formula

CO-X-CH2CH2-N(CHj)2 CO-X-CH 2 CH 2 -N (CHj) 2

CH,CH,

in der X die Gruppe —O— oder —NH- bedeutet, und deren Salze.in which X denotes the group —O— or —NH-, and their salts.

Die Erfindung betrifft weiterhin ein Verfahren zur Herstellung der Verbindungen der vorgenannten Art, das dadurch gekennzeichnet ist, daß man jeweils in an sich bekannter Weise ein reaktionsfähiges Derivat der 3,5-Dimethylbenzoesäure mit 2-(Dimethylamino)-äthanol oder Ν,Ν-Dimethyl-äthylendiamin in einem Lösungsmittel umsetzt, das Reaktionsprodukt nach dem Alkalischmachen extrahiert und wie üblich aufarbeitetThe invention further relates to a process for the production of the compounds of the aforementioned type, which is characterized in that in each case a reactive derivative of the 3,5-dimethylbenzoic acid with 2- (dimethylamino) ethanol or Ν, Ν-dimethyl-ethylenediamine in a solvent converts, the reaction product extracted after making alkaline and worked up as usual

Die Synthese dieser Produkte basiert auf der Reaktion eines aktivierten Derivats der Säure, wie des Chlorids oder Anhydrids, mit dem entsprechenden Äthylaminderivat in einem Lösemittel, Behandeln des erhaltenen Produktes mit einer Base und Extraktion mit Hilfe eines Lösungsmittels, Trocknung und Eliminierung des Lösungsmittels sowie Destillation oder Kristallisation des verbleibenden Produktes.The synthesis of these products is based on the reaction of an activated derivative of the acid, such as des Chloride or anhydride, with the corresponding ethylamine derivative in a solvent, treating the obtained product with a base and extraction with the aid of a solvent, drying and elimination of the solvent and distillation or crystallization of the remaining product.

Nachstehend wird die Erfindung anhand von Ausführungsbeispielen erläutert.The invention is explained below on the basis of exemplary embodiments.

2020th

2525th

3030th

3535

5050

Beispiel 1 (X = O)Example 1 (X = O)

In einen 2-Halskolben einer Kapazität von 100 ml, ausgestattet mit einem elektromagnetischen Rührwerk, Rückflußkühler mit Calciumchlorid-Kältemittelrohr sowie einem mit Hahn versehenen Trichter, werden 8,4 g (0,05 Mol) 3,5-DimethylbcnzoylchIorid in 40 ml trockenem Aceton gegeben. Zu dieser Lösung werden aus dem Zulauftrichter tropfenweise und unter Rühren 4,5 g(0,05 Mol) 2-(Dimelhylamino)- äthanol in 20 ml trockenem Aceton hinzugefügt Die Reaktion ist exotherm; nach Beendigung der Zugabe wird der Rückfluß zv.ei Stunden aufrechterhalten. Nach Abkühlung der Lösung wird Filtriert und die feste Masse in Wasser gelöst Es wird mit 10%iger Natronlauge alkalisiert und mit Äther extrahiert Der ätherische Extrakt wird mit wasserfreiem Epsomsalz (Magnesiumsulfat) getrocknet, filtriert der Äther im Vakuum abgezogen und das abgeschiedene Öl bei vermindertem Druck destilliertIn a 2-neck flask with a capacity of 100 ml, equipped with an electromagnetic stirrer, reflux condenser with calcium chloride refrigerant pipe as well a funnel fitted with a stopcock, 8.4 g (0.05 mol) of 3,5-dimethylbenzoyl chloride in 40 ml of dry Given acetone. 4.5 g (0.05 Mol) 2- (Dimelhylamino) - ethanol in 20 ml of dry acetone added The reaction is exothermic; after When the addition is complete, the reflux is maintained for two hours. After the solution has cooled down is filtered and the solid mass is dissolved in water. It is made alkaline with 10% sodium hydroxide solution and ether extracted The essential extract is dried with anhydrous Epsom salt (magnesium sulfate), filtered the ether is stripped off in vacuo and the oil which has separated out is distilled under reduced pressure

Das entstandene 2-(Dimethylamino)-äthyl-3',5'-dimethylbenzoat ist eine farblose Flüssigkeit vom Siedepunkt 121 -22°C/1,5 Torr.The resulting 2- (dimethylamino) ethyl 3 ', 5'-dimethylbenzoate is a colorless liquid from Boiling point 121 -22 ° C / 1.5 Torr.

Analyse:Analysis:

Berechnet für CuHi9NO2:Calculated for CuHi 9 NO 2 :

C 70,55, H 8,65, N 6,32;
gefunden:C 70.55, H 8.65, N 6.32;
found:

C 70,76, H 8,92, N 6,45.
Hydrochlorid Fp. 187-9°C(Dioxan).C 70.76, H 8.92, N 6.45.
Hydrochloride m.p. 187-9 ° C (dioxane).

Beispiel 2(X = NH)Example 2 (X = NH)

In einen 2-Halskolben einer Kapazität von 100 ml, ausgestattet mit einem elektromagnetischen Rührwerk, Rückflußkühler mit Calciumchlorid-Kältemittelrohr sowie einem Zulauftrichter werden 8,4 g (0,05MoI) 3,5-DimethylbenzoylchIorid in 40 ml trockenem Aceton gegeben. Zu dieser Lösung werden aus dem Zulauftrichter tropfenweise unter Rühren 4,4 g (0,05 Mol) Ν,Ν-Dimethyl-äthylendiamin in 20 ml trockenem Aceton hinzugefügt Die Reaktion ist exotherm. Nach Beendigung der Zugabe wird der Rückfluß während zwei Stunden aufrechterhalten, das Aceton abgedampft und der Rückstand in 50 ml 10%iger Natronlauge und 50 ml Äther aufgenommen. Die ätherische Schicht wird abgegossen, mit wasserfreiem Epsomsalz getrocknet, filtriert und der Äther unter Vakuum abgezogen. Das abgeschiedene Öl wird unter vermindertem Druck destilliert.In a 2-necked flask with a capacity of 100 ml, equipped with an electromagnetic stirrer, The reflux condenser with a calcium chloride refrigerant pipe and a feed funnel are 8.4 g (0.05MoI) 3,5-dimethylbenzoyl chloride in 40 ml of dry acetone given. 4.4 g (0.05 mol) of Ν, Ν-dimethylethylenediamine are added dropwise to this solution from the feed funnel with stirring added in 20 ml of dry acetone. The reaction is exothermic. After completion the addition, the reflux is maintained for two hours, the acetone evaporated and the residue was taken up in 50 ml of 10% sodium hydroxide solution and 50 ml of ether. The ethereal layer will Poured off, dried with anhydrous Epsom salt, filtered and the ether stripped off under vacuum. That deposited oil is distilled under reduced pressure.

Das gewonnene N-(2-Dimethylaminoäthyi)-3,5-dimethylbenzamid ist eine farblose Flüssigkeit vom Siedepunkt 160-62° C/1,5 Torr.The N- (2-Dimethylaminoäthyi) -3,5-dimethylbenzamide obtained is a colorless liquid with a boiling point of 160-62 ° C / 1.5 Torr.

Analyse:Analysis:

Berechnet für C13H2ON2O:Calculated for C 13 H 2 ON 2 O:

C 70,87, H 9,15, N 12,71;
gefunden:C 70.87, H 9.15, N 12.71;
found:

C 70,62, H 9,15, N 12,75.C 70.62, H 9.15, N 12.75.

Hydrochlorid Fp. 135 -136° C (Chloroform/Äther).Hydrochloride mp 135-136 ° C (chloroform / ether).

Claims (2)

Patentansprüche:Patent claims: 1. Aminoalkylderivate der 3,5-Dimethylbenzoesäure der allgemeinen Formel1. Aminoalkyl derivatives of 3,5-dimethylbenzoic acid the general formula CHCH - X-CH2CH2-N(CH3J2 - X-CH 2 CH 2 -N (CH 3 J 2 in der X die Gruppe —O— oder -NH- bedeutet, und deren Salze.in which X denotes the group —O— or -NH-, and their salts. 2. Verfahren zur Herstellung der Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß man Jeweils in an sich bekannter Weise ein reaktionsfähiges Derivat der 3,5-Dimethylbenzoesäure mit 2-(Dimechylamino)-äthanol oder N,N-DimethyI-äthylendiamin in einem Lösungsmittel umsetzt, das Reaktionsprodukt nach dem Alkalischmachen extrahiert und wie üblich aufarbeitet2. Process for the preparation of the compounds according to claim 1, characterized in that one In each case, in a manner known per se, a reactive derivative of 3,5-dimethylbenzoic acid with 2- (Dimechylamino) ethanol or N, N-DimethyI-ethylenediamine in a solvent which Extracted reaction product after making it alkaline and worked up as usual 1515th
DE2335079A 1973-02-21 1973-07-10 Aminoalkyl derivatives of 3,5-dimethylbenzoic acid and their salts and processes for their preparation Expired DE2335079C3 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ES411876A ES411876A1 (en) 1973-02-21 1973-02-21 A method for the industrial production of derivatives of the 3,5-dimethylenzoic acid. (Machine-translation by Google Translate, not legally binding)
FR7425241A FR2278326A1 (en) 1973-02-21 1974-07-19 2'-Aminoethyl 3,5'-dimethyl (thio)benzoates - as anti-ulcerogenic agents
BE146967A BE818112A (en) 1973-02-21 1974-07-25 PROCESS FOR THE PRODUCTION OF NEW ACID DERIVATIVES

Publications (3)

Publication Number Publication Date
DE2335079A1 DE2335079A1 (en) 1974-09-19
DE2335079B2 DE2335079B2 (en) 1978-06-15
DE2335079C3 true DE2335079C3 (en) 1979-02-15

Family

ID=27158525

Family Applications (1)

Application Number Title Priority Date Filing Date
DE2335079A Expired DE2335079C3 (en) 1973-02-21 1973-07-10 Aminoalkyl derivatives of 3,5-dimethylbenzoic acid and their salts and processes for their preparation

Country Status (3)

Country Link
BE (1) BE818112A (en)
DE (1) DE2335079C3 (en)
FR (1) FR2278326A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL57859A (en) * 1978-08-10 1983-02-23 Robins Co Inc A H Salts of benzene and thiophenecarbothioic acid 2-aminoalkyl esters and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
FR2278326B1 (en) 1977-03-11
FR2278326A1 (en) 1976-02-13
DE2335079A1 (en) 1974-09-19
BE818112A (en) 1975-01-27
DE2335079B2 (en) 1978-06-15

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