CH152790A - Process for the preparation of 3-diethylamino-2-dimethyl-1-o-aminobenzoyloxypropane. - Google Patents
Process for the preparation of 3-diethylamino-2-dimethyl-1-o-aminobenzoyloxypropane.Info
- Publication number
- CH152790A CH152790A CH152790DA CH152790A CH 152790 A CH152790 A CH 152790A CH 152790D A CH152790D A CH 152790DA CH 152790 A CH152790 A CH 152790A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- diethylamino
- preparation
- aminobenzoyloxypropane
- diethyl
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 3-Diäthylamino-2-dimethyl-l-o-aminobenzoylotypropan. Es wurde gefunden, dass die aromatischen Ester der Aminoalkohole von der Formel
EMI0001.0003
(wobei R Alkyl, R' Wasserstoff oder Alkyl bedeutet), als Mittel zur örtlichen Schmerz betäubung besonders günstige Eigenschaften zeigen.
Die als Ausgangsstoffe dienenden Alko holbasen entstehen aus Aldehydbasen, welche durch Kondensation von Aldehyden der allge meinen Formel
EMI0001.0008
mit Formalde hyd und primären oder sekundären aliphatischen Aminen erhalten werden, durch Reduktion zum Beispiel mit Natriumamalgam in schwach essigsaurer Lösung. Bei der Einwirkung von aromat=.3hen Säuren oder Derivaten, vorzugs weise von Säurechloriden, auf die Alkohol basen entstehen glatt und mit guter Aus beute die Ester, welche gut kristallisierte, auch in heissem Wasser beständige Hydro- chloride bilden.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von 3- Diäthylamino - 2 - dimethyl-1- o-aminobenzoyl- oxypropan, welches dadurch gekennzeich net ist, dass man auf 3-Diäthylamino-2- dimethyl - propan -1- o1 o-Nitrobenzoylchlorid einwirken lässt und die entstandene Nitro- verbindung reduziert.
Das 3-Diäthylamino-2-ditnethyl-l-o-amitio- benzoyloxypropan bildet mit Säuren in Wasser leicht lösliche Salze. Das gut kri stallisierte Hydrochlorid schmilzt bei 130 .
Die neue Verbindung soll in Form ihrer Salze der anästhesierenden Wirkungen wegen in der Heilkunde Verwendung finden. <I>Beispiel:</I> Man löst 212 Teile 3-Diäthylamitto-2- dimethylpropatt-l-ol itt <B>318</B> Teilen Chloro form und lässt eine Lösung von 246 Teilen o-Nitrobenzoylehlorid in 500 Teilen Chloro form unter Kühlung zutropfen. Nach mehr stündigem Stehen wird das Chloroform ab- destilliert.
Das Hydrochlorid des o-Nitroben- zoesäureesters des Diäthylainino-dimethyl-pro- pariols hinterbleibt als ein in Wasser leicht lösliches Öl. Durch Reduktion mit Zinn- chlorür und Salzsäure gewinnt man daraua in üblicher Weise die o-Aminoverbindung, deren Hydrochlorid aus Aceton mit dem Schmelzpunkt 130 kristallisiert.
Process for the preparation of 3-diethylamino-2-dimethyl-l-o-aminobenzoylotypropane. It has been found that the aromatic esters of the amino alcohols of the formula
EMI0001.0003
(where R is alkyl, R 'is hydrogen or alkyl), show particularly favorable properties as an agent for local pain relief.
The alcohol bases used as starting materials arise from aldehyde bases, which my general formula by condensation of aldehydes
EMI0001.0008
with formaldehyde and primary or secondary aliphatic amines can be obtained, for example, by reduction with sodium amalgam in weakly acetic acid solution. When aromatic acids or derivatives, preferably acid chlorides, act on the alcohol bases, the esters are formed smoothly and with good yield, which crystallize well and form hydrochlorides which are stable even in hot water.
The present invention relates to a process for the preparation of 3-diethylamino-2-dimethyl-1- o-aminobenzoyl- oxypropane, which is characterized in that 3-diethylamino-2-dimethyl-propane -1- o1 o- Allow nitrobenzoyl chloride to act and reduce the resulting nitro compound.
The 3-diethylamino-2-diethyl-l-o-amitio-benzoyloxypropane forms salts which are easily soluble in water with acids. The well-crystallized hydrochloride melts at 130.
The new compound is to be used in medicine in the form of its salts because of its anesthetic effects. <I> Example: </I> Dissolve 212 parts of 3-diethylamitto-2-dimethylpropatt-l-ol itt <B> 318 </B> parts of chloroform and leave a solution of 246 parts of o-nitrobenzoyl chloride in 500 parts of chloro drop the mold while cooling. After standing for more hours, the chloroform is distilled off.
The hydrochloride of the o-nitrobenzoic acid ester of diethylainino-dimethyl-propariol remains as an oil which is easily soluble in water. The o-amino compound, the hydrochloride of which crystallizes from acetone with a melting point of 130, is then obtained in the usual way by reduction with tin chloride and hydrochloric acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH149837T | 1929-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH152790A true CH152790A (en) | 1932-02-15 |
Family
ID=80520130
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149837D CH149837A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-diethylamino-2-dimethyl-1-p-aminobenzoyloxypropane. |
| CH152790D CH152790A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-diethylamino-2-dimethyl-1-o-aminobenzoyloxypropane. |
| CH152789D CH152789A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-isopropyl-1-p-aminobenzoyloxypropane. |
| CH152788D CH152788A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-dimethyl-1-p-aminobenzoyloxypropane. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149837D CH149837A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-diethylamino-2-dimethyl-1-p-aminobenzoyloxypropane. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH152789D CH152789A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-isopropyl-1-p-aminobenzoyloxypropane. |
| CH152788D CH152788A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-dimethyl-1-p-aminobenzoyloxypropane. |
Country Status (1)
| Country | Link |
|---|---|
| CH (4) | CH149837A (en) |
-
1930
- 1930-09-10 CH CH149837D patent/CH149837A/en unknown
- 1930-09-10 CH CH152790D patent/CH152790A/en unknown
- 1930-09-10 CH CH152789D patent/CH152789A/en unknown
- 1930-09-10 CH CH152788D patent/CH152788A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH152789A (en) | 1932-02-15 |
| CH152788A (en) | 1932-02-15 |
| CH149837A (en) | 1931-09-30 |
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