CH117493A - Process for the preparation of p-N-B-methoxyethylaminobenzoic acid-B-piperidinoethyl ester. - Google Patents
Process for the preparation of p-N-B-methoxyethylaminobenzoic acid-B-piperidinoethyl ester.Info
- Publication number
- CH117493A CH117493A CH117493DA CH117493A CH 117493 A CH117493 A CH 117493A CH 117493D A CH117493D A CH 117493DA CH 117493 A CH117493 A CH 117493A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- ester
- preparation
- methoxyethylaminobenzoic
- piperidinoethyl
- Prior art date
Links
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von p-N-g-Methogyäthylaminobenzoesäure- p-piperidinoäthylester. Es wurde gefunden, dass man durch Ein wirkung von P-Halogenäthylmethyläther auf p-Aminobenzoesäure-p-piperidinoäthylester zu dem p-N-P-Methoxyäthylaminobenzoesäure-R- piperidinoäthylester gelangt, der in Form seiner Salze, wie umfangreiche Vergleichsversuche der Anmelderin ergeben haben,
bezüglich der Stärke seiner Wirkung das Kokain um ein Vielfaches übertrifft. Das neue Produkt ist ein typisches Oberflächenanästhetikum und kommt also für das grosse Gebiet der Schleimhaut anästhesie in erster Linie in Frage. Der basische Ester ist ein helles 01;
das Chlor hydrat besteht aus farblosen Kristallen vom Schmelzpunkt<B>1380,</B> löst sich in Wasser mit neutraler Reaktion und besitzt ein ausser ordentlich starkes Anästhesierungsvermögen. Beispiel Aequimolekulare Mengen p-Aminobenzoe- säure-@-piperidinoäthylester F. 90 (Deutsche Patentschrift 172568 der Klasse 12 q) und ss-Jodäthylmethyläther Kp. 154-155 werden zusammen 10 Stunden auf dem - Wasserbade erhitzt. Danach wird das Produkt in Wasser gelöst und die wenn nötig vom Ungelösten filtrierte Lösung mit verdünnter Natrium karbonatlösung übersättigt.
Dadurch wird der Alkaminester als 01 abgeschieden, während nebenher gebildete quaternäre Ammoniumsalze in Lösung bleiben. Nach dem Aufnehmen in Äther und Trocknen der Ätherlösung über Kaliumkarbonat erhält man durch fraktionierte Destillation im Vakuum bei 4 mm Druck eine oberhalb 200' siedende Fraktion, die mit der für 1 Mol. berechneten Menge Salzsäure in Äthylalkohol versetzt auf Zugabe von Äther erst öliges, aber bald fest werdendes p-N-,Q Methoxyäthylaminobenzoesäure-ss-piperidino- äthylestermonohydrochlorid ergibt,
das durch Umkristallisieren aus Alkohol-Essigestermi- sehung rein vom Schmelzpunkt<B>1380</B> erhalten wird.
Process for the preparation of p-N-g-Methogyäthylaminobenzoäure- p-piperidinoäthylester. It has been found that an action of P-haloethyl methyl ether on p-aminobenzoic acid p-piperidinoethyl ester leads to the p-N-P-methoxyethylaminobenzoic acid R-piperidinoethyl ester, which in the form of its salts, as extensive comparative tests by the applicant have shown,
exceeds cocaine many times over in terms of the strength of its effects. The new product is a typical surface anesthetic and is therefore primarily suitable for the large area of the mucosal anesthesia. The basic ester is a light 01;
The chlorine hydrate consists of colorless crystals with a melting point of <B> 1380 </B>, dissolves in water with a neutral reaction and has an extremely strong anesthetic ability. Example Equimolecular amounts of p-aminobenzoic acid - @ - piperidinoethyl ester F. 90 (German patent 172568 class 12 q) and ß-iodoethyl methyl ether, boiling point 154-155, are heated together for 10 hours on the water bath. The product is then dissolved in water and the solution, filtered from undissolved material if necessary, is supersaturated with dilute sodium carbonate solution.
As a result, the alkamine ester is deposited as oil, while quaternary ammonium salts formed at the same time remain in solution. After the ether solution has been taken up in ether and dried over potassium carbonate, fractional distillation in vacuo at 4 mm pressure gives a fraction boiling above 200 ', which is mixed with the amount of hydrochloric acid in ethyl alcohol calculated for 1 mol soon solidifying pN-, Q methoxyethylaminobenzoic acid-SS-piperidino ethyl ester monohydrochloride results,
which is obtained by recrystallization from alcohol-ethyl acetate mixture with a purely melting point of <B> 1380 </B>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH113055T | 1925-01-06 | ||
| CH117493T | 1925-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH117493A true CH117493A (en) | 1926-11-01 |
Family
ID=25708100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH117493D CH117493A (en) | 1925-01-06 | 1925-01-06 | Process for the preparation of p-N-B-methoxyethylaminobenzoic acid-B-piperidinoethyl ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH117493A (en) |
-
1925
- 1925-01-06 CH CH117493D patent/CH117493A/en unknown
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