CH149837A - Process for the preparation of 3-diethylamino-2-dimethyl-1-p-aminobenzoyloxypropane. - Google Patents
Process for the preparation of 3-diethylamino-2-dimethyl-1-p-aminobenzoyloxypropane.Info
- Publication number
- CH149837A CH149837A CH149837DA CH149837A CH 149837 A CH149837 A CH 149837A CH 149837D A CH149837D A CH 149837DA CH 149837 A CH149837 A CH 149837A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- diethylamino
- water
- preparation
- aminobenzoyloxypropane
- Prior art date
Links
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- 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-Diätbylamino-2-dimethyl-l-p-aminobetizoyloxypropan. Es wurde gefunden, dass die aromatischen Ester,der Aminoalkoliole von der Formel
EMI0001.0005
(wobei R Alkyl, R' Wasserstoff oder Alkyl bedeutet), als Mittel zur örtlichen Schmerz betäubung besonders günstige Eigenschaften zeigen.
Die als Ausgangsstoffe dienenden Alkollolbasen entstehen aus Aldehydbasen, welche durch Kondensation von Aldeliyden der allgemeinen Formel
EMI0001.0011
mit Formaldeliyd und primären oder sekundären aliphatischen Aminen erhalten weerden, durch Redaktion zum Beispiel mit Natriumamal- gam in schwach essigsaurer Lösung.
Bei der Einwirkung von aromatischen Säuren oder Derivaten, vorzugsweise von Säureelilo- riden, auf die Alkoholbasen entstellen glatt und mit guter Ausbeute die Ester, welche gut kristallisierte, auch in heissem Wasser beständige lIydrochloride bilden.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von<B>3-Di-</B> äthylamino-92-dimethyl-l-p-aminobenzoyloxy- propan, welches dadurch gekennzeichnet ist. dass man auf 3-Diäthylamino-9--dimüthyl-pro- pan <B>- 1 -</B> ol <B>p -</B> Nitrobenzoylehlorid einwirken lässt und die entstandene Nitroverbindung reduziert.
Das<B>3 -</B> Diäthylamino <B>-</B> 2<B>-</B> dimethyl <B>- 1 -</B> p- a,minobenzoylo.xypropan bildet. farblose Kri stalle vom Schmelzpunkt<B>53-54'.</B> Es löst sieh leicht in den- meisten organischen Lö sungsmitteln, wie Alkohol und Äther,<B>in</B> Wasser ist es unlöslich. Leicht löslich in Wasser ist das gut kristallisierende Hydro- chlorid, welches bei<B>196-197 '</B> schmilzt. Seine wässerigen Lösungen sind beständig.
Die neue Verbinduno- soll in Form ihrer Salze der anästliesierenden Wirkungen wegen in der Heilkunde Verwendung finden. <I>Beispiel:</I> Fügt man eine Lösung von<B>5.5</B> Tellen p- Nitrobenzoylehlorid in Chloroform zu 4 Tei len 3-Diäthylamino-2-dimetbyl-propaii-l-ol, so bildet sich unter Erwärmung das Hydro- chlorid des 3-Diäthylamino-2-dimethyl-l-p- nitrob(-,nzoyloxypropans. Man lässt einige Stunden stehen,
fällt die gebildete Verbin- dulic, mit Äther aus und kristallisiert sie aus Isopropylalkoliol um. Schmelzpunkt<B>160</B> <B>1</B> Teil dieses Zwischenproduktes wird in<B>15</B> Teilen Wasser gelöst und nach Zusatz von <B>0,3</B> Teilen einer 1%igen Palladiumehloriir- lösung -und<B>0,1</B> Teil Tierkohle bei 2 Atmo sphären Druck hydriert. Nach beendigter #Vasserstoffaufnahme wird filtriert und die Lösung im Vakuum eingeengt. Der Rück stand wird aus Isopropylalkohol umkristal lisiert.
Aus der Base wird mit alkoholischer Salzsäure und Äther das 3-Diäthylamino-2 (limeithyl-l-p-aminobenzovloxypropanhydro- chlorid, welches bei<B>196-197 '</B> schmilzt, er halten.
Process for the preparation of 3-dietbylamino-2-dimethyl-1-p-aminobetizoyloxypropane. It has been found that the aromatic esters, the amino alcohols of the formula
EMI0001.0005
(where R is alkyl, R 'is hydrogen or alkyl), show particularly favorable properties as agents for local pain relief.
The alcohol bases used as starting materials arise from aldehyde bases, which are formed by condensation of aldeliyden of the general formula
EMI0001.0011
with formaldehyde and primary or secondary aliphatic amines, for example by editing with sodium amalgam in a weakly acetic acid solution.
When aromatic acids or derivatives, preferably acid elilorides, act on the alcohol bases, the esters disfigure 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-di- ethylamino-92-dimethyl-1-p-aminobenzoyloxypropane, which is characterized. that 3-diethylamino-9 - dimethylpropane <B> - 1 - </B> ol <B> p - </B> nitrobenzoylechloride is allowed to act and the resulting nitro compound is reduced.
The <B> 3 - </B> diethylamino <B> - </B> 2 <B> - </B> dimethyl <B> - 1 - </B> p- a, minobenzoylo.xypropane forms. colorless crystals with a melting point of <B> 53-54 '. </B> It dissolves easily in most organic solvents such as alcohol and ether, and <B> in </B> water it is insoluble. The readily crystallizing hydrochloride is easily soluble in water and melts at <B> 196-197 '</B>. Its aqueous solutions are permanent.
The new compound should be used in medicine in the form of its salts because of its anesthetic effects. <I> Example: </I> If a solution of <B> 5.5 </B> parts of p-nitrobenzoylechloride in chloroform is added to 4 parts of 3-diethylamino-2-dimethyl-propai-l-ol, then under Warming the hydrochloride of 3-diethylamino-2-dimethyl-lp-nitrob (-, nzoyloxypropane. It is left to stand for a few hours,
the compound formed precipitates out with ether and recrystallizes it from isopropyl alcohol. Melting point <B> 160 </B> <B> <B> 1 </B> part of this intermediate product is dissolved in <B> 15 </B> parts of water and, after the addition of <B> 0.3 </B> parts of a 1 % palladium chloride solution and <B> 0.1 </B> part of animal charcoal hydrogenated at 2 atmospheric pressure. After the uptake of hydrogen has ended, it is filtered and the solution is concentrated in vacuo. The residue is recrystallized from isopropyl alcohol.
3-Diethylamino-2 (limeithyl-1-p-aminobenzovloxypropane hydrochloride, which melts at <B> 196-197 '</B>, is obtained from the base with alcoholic hydrochloric acid and ether.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH149837T | 1929-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH149837A true CH149837A (en) | 1931-09-30 |
Family
ID=80520130
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH152788D CH152788A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-dimethyl-1-p-aminobenzoyloxypropane. |
| CH152789D CH152789A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-isopropyl-1-p-aminobenzoyloxypropane. |
| CH152790D CH152790A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-diethylamino-2-dimethyl-1-o-aminobenzoyloxypropane. |
| CH149837D CH149837A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-diethylamino-2-dimethyl-1-p-aminobenzoyloxypropane. |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH152788D CH152788A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-dimethyl-1-p-aminobenzoyloxypropane. |
| CH152789D CH152789A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-isopropyl-1-p-aminobenzoyloxypropane. |
| CH152790D CH152790A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-diethylamino-2-dimethyl-1-o-aminobenzoyloxypropane. |
Country Status (1)
| Country | Link |
|---|---|
| CH (4) | CH152788A (en) |
-
1930
- 1930-09-10 CH CH152788D patent/CH152788A/en unknown
- 1930-09-10 CH CH152789D patent/CH152789A/en unknown
- 1930-09-10 CH CH152790D patent/CH152790A/en unknown
- 1930-09-10 CH CH149837D patent/CH149837A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH152788A (en) | 1932-02-15 |
| CH152790A (en) | 1932-02-15 |
| CH152789A (en) | 1932-02-15 |
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