CH110426A - Process for the preparation of an alkamine ester of an aromatic aminocarboxylic acid. - Google Patents
Process for the preparation of an alkamine ester of an aromatic aminocarboxylic acid.Info
- Publication number
- CH110426A CH110426A CH110426DA CH110426A CH 110426 A CH110426 A CH 110426A CH 110426D A CH110426D A CH 110426DA CH 110426 A CH110426 A CH 110426A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- alkamine
- aminocarboxylic acid
- aromatic aminocarboxylic
- ester
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title description 2
- 125000003118 aryl group Chemical group 0.000 title description 2
- XMMRNCHTDONGRJ-ZZXKWVIFSA-N 4-nitrocinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C([N+]([O-])=O)C=C1 XMMRNCHTDONGRJ-ZZXKWVIFSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YWIQQKOKNPPGDO-UHFFFAOYSA-N 2,3-didehydrophenylalanine zwitterion Chemical compound OC(=O)C(N)=CC1=CC=CC=C1 YWIQQKOKNPPGDO-UHFFFAOYSA-N 0.000 description 1
- RUPXNPWALFDXJD-UHFFFAOYSA-N 3-(4-nitrophenyl)prop-2-enoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C=CC(Cl)=O)C=C1 RUPXNPWALFDXJD-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Alkaminesters einer aromatischen Aminokarbonsäure. Es wurde gefunden, dass der bisher unbekannte Aminozimtsäurealkaminester von der Formel
EMI0001.0004
ein wertvolles Anaestheticum darstellt.
Man stellt den neuen Ester durch Ver- esterung des Alkamins mit p-Nitrozimtsäure und nachfolgende Reduktion dar.
<I>Beispiel:</I> 131 Gewichtsteile a-Dimethylainino-,p- methyl-r-oxybutan werden mit<B>500</B> Gewichts teilen Benzol vermischt und diese Mischung zu einer Lösung von 211,5 Gewichtsteilen p-Nitrozimtsäurechlorid in<B>500</B> Gewichtsteilen Benzol unter Rühren zugegeben. Die Mischung wird einige Munden lang gekocht, dann mit Wasser versetzt und die wässerige Lösung vom Benzol getrennt. Aus der wässerigen Lösung wird die Nitrobase mit Alkali als Öl abgeschieden. Das Öl wird in Salzsäure gelöst und die Lösung reduziert.
Das a-Dirnethylamino-p-methyl-r-(p-amino- cinnamoyl)-oxybutan stellt ein dickes Öl dar, das bei 230-235 unter 8 mm Druck siedet. Das Monochlorhydrat bildet ein mikrokristal linisches Pulver, das stark anaesthesiert.
Process for the preparation of an alkamine ester of an aromatic aminocarboxylic acid. It has been found that the hitherto unknown aminocinnamate of the formula
EMI0001.0004
represents a valuable anesthetic.
The new ester is produced by esterification of the alkamine with p-nitrocinnamic acid and subsequent reduction.
<I> Example: </I> 131 parts by weight of a-dimethylainino-, p-methyl-r-oxybutane are mixed with <B> 500 </B> parts by weight of benzene and this mixture is mixed to a solution of 211.5 parts by weight of p- Nitrocinnamic acid chloride in <B> 500 </B> parts by weight of benzene was added with stirring. The mixture is boiled for a few mouths, then water is added and the aqueous solution is separated from the benzene. The nitro base with alkali is deposited as an oil from the aqueous solution. The oil is dissolved in hydrochloric acid and the solution is reduced.
The a-dirnethylamino-p-methyl-r- (p-aminocinnamoyl) -oxybutane is a thick oil that boils at 230-235 under 8 mm pressure. The monochlorohydrate forms a microcrystalline, linear powder that is strongly anesthetized.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH108820T | 1923-09-13 | ||
| CH110426T | 1923-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH110426A true CH110426A (en) | 1925-06-01 |
Family
ID=25707453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH110426D CH110426A (en) | 1923-09-13 | 1923-09-13 | Process for the preparation of an alkamine ester of an aromatic aminocarboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH110426A (en) |
-
1923
- 1923-09-13 CH CH110426D patent/CH110426A/en unknown
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