DE935130C - Process for the preparation of alkyl or alkoxalkylaminobenzoic acid esters - Google Patents
Process for the preparation of alkyl or alkoxalkylaminobenzoic acid estersInfo
- Publication number
- DE935130C DE935130C DEF10969A DEF0010969A DE935130C DE 935130 C DE935130 C DE 935130C DE F10969 A DEF10969 A DE F10969A DE F0010969 A DEF0010969 A DE F0010969A DE 935130 C DE935130 C DE 935130C
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- alkoxalkylaminobenzoic
- preparation
- carboxylic acid
- acid esters
- 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
- 125000000217 alkyl group Chemical group 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 5
- 150000002148 esters Chemical class 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- -1 carboxylic acid halide radical Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 150000005417 aminobenzoic acid derivatives Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000005440 nitrobenzoic acid derivatives Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000005415 aminobenzoic acids Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- GTXRSQYDLPYYNW-UHFFFAOYSA-N ethyl 4-(butylamino)benzoate Chemical compound CCCCNC1=CC=C(C(=O)OCC)C=C1 GTXRSQYDLPYYNW-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Alkyl- bzw. Alkoxalkylaminobenzoesäureestern
Die nach diesem Verfahren gewonnenen Verbindungen zeichnen sich gegenüber bekannten Alkaminestern von N-m,onoallcyliert@en oder N-monoall::yloxalkylierten p-Aminobenzoesäuren dadurch aus, daß sie neben hervorragender lokalanästhetischerWirkung infolge ihrer völligen Reizlosigkeit ganz ausgezeichnete Oberfläclienanästhetil:a sind.The compounds obtained by this process are opposed to one another known alkamine esters of N-m, monoallcylated @ en or N-monoall :: yloxalkylated p-aminobenzoic acids in that they have an excellent local anesthetic effect Surface anesthetics are excellent as a result of their complete lack of irritation: a are.
In weiterer Ausgestaltung des Verfahrens wurde nun gefunden, daß man zu weiteren neuen wertvollen Verbindungen gelangt, wenn man i-Aminopropandiole der allgemeinen Formel wobei R, Wasserstoff, Alkyl, Alkoxalkyl oder Aralkyl und R2 Cycloalkyl bedeutet, entweder mit Aminobenzoesäurederivaten der allgemeinen Formel wobei X einen Carbonsäure-, Carbonsäureester-oder Carbonsäurehalogenidrest bedeutet, R3 für Wasserstoff, Alkyl oder Alkoxalkyl und R4 für Alkyl oder Alkoxalkyl steht, in Gegenwart von Metallalkoholat kondensiert oder die Kondensation mit den entsprechenden Nitrobenzoesäurederivaten durchführt, anschließend reduziert, die Reduktionsprodukte mit i Mol Alkylierungs- bzw. Alkoxalkylierungsmittel umsetzt und einen gegebenenfalls in der aliphatischen Aminogruppe vorhandenen Benzylrest reduktiv abspaltet.In a further embodiment of the process, it has now been found that further new valuable compounds are obtained if i-aminopropanediols of the general formula are used where R is hydrogen, alkyl, alkoxalkyl or aralkyl and R2 is cycloalkyl, either with aminobenzoic acid derivatives of the general formula where X is a carboxylic acid, carboxylic ester or carboxylic acid halide radical, R3 is hydrogen, alkyl or alkoxyalkyl and R4 is alkyl or alkoxyalkyl, condensed in the presence of metal alcoholate or the condensation with the corresponding nitrobenzoic acid derivatives is carried out, then reduced, the reduction products with 1 mol of alkylation - or alkoxalkylating agents and reductively splitting off any benzyl radical which may be present in the aliphatic amino group.
Die erhaltenen Verbindungen sind wie die im Hauptpatent genannten Verbindungen hervorragende Lokalanästhetika und Oberflächenanästhetika, da sie völlig reizlos sind.The compounds obtained are like those mentioned in the main patent Compounds excellent local anesthetics and surface anesthetics as they are totally are irritating.
Beispiel 409 p-Butylaminobenzoesäureäthylester und 409 i-Cyclohexylbenzylaminopropandiol-(z, 3) werden mit 5 ccm 5o/oiger Natriummethylatlösung 2 Stunden auf 12o' erhitzt. Das Reaktionsprodukt wird in Essigester und verdünnter Essigsäure aufgenommen, dann mit verdünnter Salzsäure durchgeschüttelt. Die salzsaure Lösung wird mit Kaliumcarbonat alkalisch gemacht und mit Essigester ausgeschütbelt. Nach dem Abdestillieren des Essigesters wird der Rückstand mit alkoholischer Salzsäure neutralisiert und in Methanol mit Palladium als Katalysator hydriert. Nach beendeter Reduktion wird das Methanol abdestilliert. Man erhält das p-Butylaminobenzoesäure-cyclohexylamino-/3-oxy-propylesterchlorhydrat vom Fp. 137 bis 139°.Example 409 ethyl p-butylaminobenzoate and 409 i-cyclohexylbenzylaminopropanediol (e.g. 3) are heated to 12 ° for 2 hours with 5 ccm of 50% sodium methylate solution. That The reaction product is taken up in ethyl acetate and dilute acetic acid, then shaken with dilute hydrochloric acid. The hydrochloric acid solution is made with potassium carbonate Made alkaline and shaken out with ethyl acetate. After distilling off the Ethyl acetate, the residue is neutralized with alcoholic hydrochloric acid and in Hydrogenated methanol with palladium as a catalyst. After the reduction is finished, this will be Methanol is distilled off. The p-butylaminobenzoic acid cyclohexylamino / 3-oxy-propyl ester chlorohydrate is obtained from m.p. 137 to 139 °.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF10969A DE935130C (en) | 1951-12-25 | 1951-12-25 | Process for the preparation of alkyl or alkoxalkylaminobenzoic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF10969A DE935130C (en) | 1951-12-25 | 1951-12-25 | Process for the preparation of alkyl or alkoxalkylaminobenzoic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE935130C true DE935130C (en) | 1955-11-10 |
Family
ID=7086608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF10969A Expired DE935130C (en) | 1951-12-25 | 1951-12-25 | Process for the preparation of alkyl or alkoxalkylaminobenzoic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE935130C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118931A (en) * | 1959-07-02 | 1964-01-21 | Ciba Geigy Corp | Polyoxyaminoalkyl aminobenzoates |
-
1951
- 1951-12-25 DE DEF10969A patent/DE935130C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118931A (en) * | 1959-07-02 | 1964-01-21 | Ciba Geigy Corp | Polyoxyaminoalkyl aminobenzoates |
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