AT157240B - Process for the preparation of tertiary acetamides substituted by unsaturated alkyl radicals. - Google Patents
Process for the preparation of tertiary acetamides substituted by unsaturated alkyl radicals.Info
- Publication number
- AT157240B AT157240B AT157240DA AT157240B AT 157240 B AT157240 B AT 157240B AT 157240D A AT157240D A AT 157240DA AT 157240 B AT157240 B AT 157240B
- Authority
- AT
- Austria
- Prior art keywords
- tertiary
- unsaturated alkyl
- alkyl radicals
- preparation
- acetamides
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von durch ungesättigte Alkylreste substituierten tertiären Acetamiden.
Unter den Schlafmitteln stellen die Amide bestimmter organischer Säuren eine sehr wichtige Gruppe dar. Es sind auch bereits tertiäre Acetamid mit starker hypnotischer Wirkung, die eine ungesättigte Alkylgruppe'am zur Carboxylgruppe -ständigen Kohlenstoffatom tragen, wie z. B. das Diäthyl- allylaeetamid und die durch Verseifung der entsprechenden Acetonitrile hergestellt wurden, bekannt (deutsche Patentschriften Nr. 412820, Nr. 473329). In der letztgenannten Patentschrift sind auch tertiäre Acetonitrile mit mehreren ungesättigten Alkylresten beschrieben.
Wie nun gefunden wurde, zeigen tertiäre Acetamide mit zwei oder drei ungesättigten Alkylresten gegenüber den bisher bekannten Schlafmitteln aber auch gegenüber den bekannten tertiären Acetamiden bei Vergleichsversuchen an Kaninchen eine erheblich stärkere Wirksamkeit. Die schlafmachende Dosis liegt bei den mehrfach ungesättigt substituierten tertiären Acetamiden bereits bei
EMI1.1
allylacetamid tritt die einschläfernde Wirkung erst bei 60 M : y je Kilogramm Kaninchen auf. Es zeigt sich ferner, dass bei den Barbitursäuren die kleinste schlafmachende Gabe von der vollnarkotisehen
EMI1.2
therapeutische Breite besteht.
Ein derartig günstiges Ergebnis war keineswegs zu erwarten, denn die Zusammenhänge zwischen Konstitution und hypnotischer Wirkung sind durchaus nicht immer so, dass eine Vervielfachung gewisser als wirksam erkannter Gruppen auch eine Verstärkung und Verbesserung der Wirkung nach sich ziehen müsste.
Die Verseifung der tertiären Acetonitrile erfolgt in an sich bekannter Weise.
Die nach vorliegendem Verfahren erhältlichen Acetamide sind in Wasser schwer löslich, lassen sich aber aus Petroläther gut umkristallisieren.
Beispiel 1 : 200 Gew.-Teile Triallylacetonitril werden in einer Lösung von 140 Gew.-Teilen Ätzkali in 1200 Raumteilen Batylalkobol 5 Stunden am Rückflusskühler gekocht. Nach Beendigung der Reaktion wird der Butylalkohol mit Wasserdampf abdestilliert ; beim Abkühlen kristallisiert der Rückstand. Nach dem Absaugen wird mit Wasser alkalifrei gewaschen, getrocknet und mehrfach aus Benzin umkristallisiert. Das erhaltene Triallylacetamid (F=63-65 ) ist leicht löslich in organischen
EMI1.3
Beispiel 3 : 300 Gew.-Teile Propyldiallylacetonitril werden in einer Lösung von 208 Gew.-Teilen Ätzkali in 1800 Raumteilen Butylalkohol 5 Stunden am Rüekflusskühler gekocht. Nach Beendigung der Reaktion wird wie im Beispiel 1 aufgearbeitet. Das erhaltene Propyldiallylaeetamid (F=53C) zeigt dasselbe chemische Verhalten wie die Amide der vorhergehenden Beispiele.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of tertiary acetamides substituted by unsaturated alkyl radicals.
Among the sleeping pills, the amides of certain organic acids represent a very important group. There are also tertiary acetamides with a strong hypnotic effect that carry an unsaturated alkyl group on the carbon atom on the carboxyl group, such as. B. the diethyl allylaeetamid and which were prepared by saponification of the corresponding acetonitrile, known (German patents No. 412820, No. 473329). The last-mentioned patent also describes tertiary acetonitriles with several unsaturated alkyl radicals.
As has now been found, tertiary acetamides with two or three unsaturated alkyl radicals are considerably more effective than the previously known sleeping pills but also compared with the known tertiary acetamides in comparative tests on rabbits. The sleep-inducing dose is already included with the polyunsaturated substituted tertiary acetamides
EMI1.1
allylacetamide does not have a drowsy effect until 60 M: y per kilogram of rabbit. It also shows that the smallest sleep-inducing dose of barbituric acids comes from full anesthesia
EMI1.2
therapeutic breadth.
Such a favorable result was by no means to be expected, because the connections between constitution and hypnotic effect are by no means always such that a multiplication of certain groups recognized as effective would also lead to a strengthening and improvement of the effect.
The tertiary acetonitriles are saponified in a manner known per se.
The acetamides obtainable by the present process are sparingly soluble in water, but can easily be recrystallized from petroleum ether.
Example 1: 200 parts by weight of triallylacetonitrile are refluxed for 5 hours in a solution of 140 parts by weight of caustic potash in 1200 parts by volume of batyl alcohol. After the reaction has ended, the butyl alcohol is distilled off with steam; the residue crystallizes on cooling. After suctioning off, it is washed alkali-free with water, dried and recrystallized several times from gasoline. The triallylacetamide obtained (F = 63-65) is easily soluble in organic
EMI1.3
Example 3: 300 parts by weight of propyldiallylacetonitrile are boiled for 5 hours on a reflux condenser in a solution of 208 parts by weight of caustic potash in 1800 parts by volume of butyl alcohol. After the reaction has ended, it is worked up as in Example 1. The propyldiallylaeetamide obtained (F = 53C) shows the same chemical behavior as the amides of the previous examples.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE157240T | 1931-05-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
AT157240B true AT157240B (en) | 1939-10-10 |
Family
ID=29412824
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT157240D AT157240B (en) | 1931-05-13 | 1932-02-09 | Process for the preparation of tertiary acetamides substituted by unsaturated alkyl radicals. |
Country Status (1)
Country | Link |
---|---|
AT (1) | AT157240B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1122939B (en) * | 1958-08-08 | 1962-02-01 | Hoechst Ag | Process for the preparation of ª,ª-alkenoic acid amides |
-
1932
- 1932-02-09 AT AT157240D patent/AT157240B/en active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1122939B (en) * | 1958-08-08 | 1962-02-01 | Hoechst Ag | Process for the preparation of ª,ª-alkenoic acid amides |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AT142251B (en) | Process for the preparation of alkamine esters. | |
AT157240B (en) | Process for the preparation of tertiary acetamides substituted by unsaturated alkyl radicals. | |
AT268233B (en) | Process for the preparation of new cyclopropanecarboxylic acid esters | |
CH369759A (en) | Process for the preparation of N-alkylpiperidine-α-carboxylic acid anilides | |
DE763489C (en) | Process for the preparation of ª-aminoethyl esters of substituted phenylacetic acids | |
DE934103C (en) | Process for the production of cyclooctylated alkyl acetic acids with a strong cholagogue effect | |
DE752871C (en) | Process for the production of basic ethers of fatty aromatic oxyates | |
DE1259635B (en) | Agility improver for diesel fuels | |
AT225359B (en) | Process for the preparation of the new 17-β-oxy-17-α-methylandrostan- (3, 2, -c) -iso-oxazole | |
AT250352B (en) | Process for the preparation of new quaternary 4-pyridylthioethers | |
AT254855B (en) | Process for the preparation of new 3-amino-2,4,6-triiodobenzoic acid derivatives | |
DE897559C (en) | Process for the preparation of diaryldialkylaethylenes | |
AT258886B (en) | Process for the preparation of new optically active or racemic 1-aryloxy-2-hydroxy-3-isopropylaminopropanes and their salts | |
AT235280B (en) | Process for the production of new indole derivatives | |
CH158981A (en) | Method for the preparation of a strongly hypnotic, unsaturated substituted tertiary acetamide. | |
AT233548B (en) | Process for the production of new asparagine derivatives | |
AT216156B (en) | Process for the preparation of polyhydrophenanthrene compounds | |
AT216497B (en) | Process for the preparation of new β-hydroxybutyric acid amide derivatives | |
AT221504B (en) | Process for the production of new basic phenol ethers and their salts | |
AT224126B (en) | Process for the preparation of the new optical isomers of 5- (3'-dimethylamino-2'-methylpropyl) -iminodibenzyl | |
AT283555B (en) | DETERGENT MIXTURES | |
DE1950329A1 (en) | Anti-trichomonas pharmaceuticals | |
CH173413A (en) | Process for the preparation of N-oxyethyl-N-B, y-dioxypropyl-aminobenzene. | |
DE1470221A1 (en) | Piperidinomethyl compounds and processes for their preparation | |
CH176155A (en) | Process for the preparation of 2-ethoxy-5-propionyl-aminopyridine. |