CH179697A - Process for the preparation of 1-tropic acid-2,2-dimethyl-3-dimethylaminopropanol ester. - Google Patents
Process for the preparation of 1-tropic acid-2,2-dimethyl-3-dimethylaminopropanol ester.Info
- Publication number
- CH179697A CH179697A CH179697DA CH179697A CH 179697 A CH179697 A CH 179697A CH 179697D A CH179697D A CH 179697DA CH 179697 A CH179697 A CH 179697A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- tropic acid
- ester
- dimethylaminopropanol
- preparation
- Prior art date
Links
Description
Verfahren zur Darstellung von 1-Tropasäure-2,2-dimethyl-3-dimethylamino- propanolester. Die Ester von Aminoalkoholen der all gemeinen Formel
EMI0001.0004
wobei R ein Alkyl und R.' ein Alkyl oder Wasserstoff bedeutet, mit aromatischen Säu ren sind sehr stark wirksame Lokalanästhe- tica.
Es wurde nun gefunden, dass in den fettaromatischen Estern dieser Ainirioalkohole die lokalanästhetische Wirkung fast völlig ztirüektritt, dass ihnen aber statt dessen eine ausserordentlich starke krampflösende Wir kung zukommt, die bei einzelnen Gliedern die Wirkung des Papaverins erheblich über trifft.
Die als Ausgangsstoffe dienenden Amino- alkohole können aus den nach den Ver fahren der Patentschriften 147156, 151127 bis 15l130, 151134 und 151135 erhaltenen Aminoaldehyden durch Reduktion mit Na triumamalgam in schwach essigsaurer Lö sung gewonnen werden.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von 1-Tropa säure-2,2-dimethyl-3-dimethylaminopropanol- ester, welches dadurch gekennzeichnet ist, dass man auf 2,2-Dimethyl-3-dimethylamino- propylhalogenide ein Salz der 1-Tropasäure einwirken lässt.
Die bisher unbekannten Halogenverbin dungen des 2,2-Dimethyl-3-dimethylamino- propanols entstehen leicht und in guter Aus beute bei der Einwirkung der üblichen Halo- genierungsmittel, wie zum Beispiel Thionyl- chlorid. Es sind farblose, im Vakuum un- zersetzt destillierbare Öle, die mit den Halogenwasserstoffsäuren feste Salze bilden.
Der 1-Tropasäure-2,2-dimethyl-3-dimethyl- aminopropanolester bildet ein farbloses Öl. Seine Salze mit Mineralsäuren sind flüssig und leicht löslich in Wasser. Das Drehungs vermögen des 1-Tropasäure-2,2-dimethyl-3- dimethylaminopropanolester-ist (a)n =-44 .
Er soll als Arzneimittel Verwendung finden.
<I>Beispiel:</I> 20 Teile trockenes 1-tropasaur-es Kalium werden mit 18 Teilen 2,2-Dimethyl-3-dime- thylaminopropylchlorid (erhalten aus Dime- thyldimethylaminopropanolhydrochlorid durch Erwärmen mit Thioriylcblorid)-und 100 Teilen Benzol 3 Stunden am Rückfluss gekocht. Man filtriert vom Rückstand ab, schüttelt mit verdünnter Salzsäure aus und fällt das Per chlorat des Esters durch Zusatz einer kon zentrierten Natriumperchloratlösung aus Öl aus.
Dieses wird abgetrennt, mit Wasser gewaschen und dann mit Äther und Natrium- carbonatlösung geschüttelt. Die Ätherlösung wird getrocknet und eingedunstet. Der 1-Tropa- säure-2,2-dimetlryl-3-dirnethylarninopropanol- ester bleibt als farbloses Öl, das schwerer ist als Wasser, zurück.
Process for the preparation of 1-tropic acid-2,2-dimethyl-3-dimethylamino-propanol ester. The esters of amino alcohols of the general formula
EMI0001.0004
where R is alkyl and R. ' denotes an alkyl or hydrogen, with aromatic acids are very effective local anesthetics.
It has now been found that in the fatty aromatic esters of these Ainirioalcohols the local anesthetic effect is almost completely reduced, but that instead they have an extraordinarily strong antispasmodic effect, which considerably exceeds the effect of papaverine in individual limbs.
The amino alcohols used as starting materials can be obtained from the amino aldehydes obtained by the methods of patents 147156, 151127 to 151130, 151134 and 151135 by reduction with sodium amalgam in weakly acetic acid solution.
The present invention relates to a process for the preparation of 1-tropic acid-2,2-dimethyl-3-dimethylaminopropanol ester, which is characterized in that a salt of 1 is added to 2,2-dimethyl-3-dimethylaminopropyl halides -Tropic acid can act.
The previously unknown halogen compounds of 2,2-dimethyl-3-dimethylaminopropanol are formed easily and in good yield when exposed to the usual halogenating agents, such as thionyl chloride. They are colorless oils that can be distilled in a vacuum without decomposing and that form solid salts with the hydrohalic acids.
The 1-tropic acid-2,2-dimethyl-3-dimethyl-aminopropanol ester forms a colorless oil. Its salts with mineral acids are liquid and easily soluble in water. The rotation capacity of 1-tropic acid-2,2-dimethyl-3-dimethylaminopropanol ester is (a) n = -44.
It should be used as a medicine.
<I> Example: </I> 20 parts of dry 1-tropic acid potassium are mixed with 18 parts of 2,2-dimethyl-3-dimethylaminopropyl chloride (obtained from dimethyldimethylaminopropanol hydrochloride by heating with thioriyl chloride) and 100 parts of benzene 3 Boiled under reflux for hours. The residue is filtered off, extracted with dilute hydrochloric acid, and the perchlorate of the ester is precipitated from oil by adding a concentrated sodium perchlorate solution.
This is separated off, washed with water and then shaken with ether and sodium carbonate solution. The ether solution is dried and evaporated. The 1-tropic acid-2,2-dimethyl-3-methylamino-propanol ester remains as a colorless oil that is heavier than water.
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE139454X | 1932-03-22 | ||
DEH136773D DE594085C (en) | 1932-03-22 | 1933-07-07 | Process for the production of basic esters of fatty acids |
CH174811T | 1934-02-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH179697A true CH179697A (en) | 1935-09-15 |
Family
ID=34068605
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH179696D CH179696A (en) | 1932-03-22 | 1934-02-06 | Process for the preparation of d-tropic acid-2,2-dimethyl-3-diethylaminopropanol ester. |
CH179697D CH179697A (en) | 1932-03-22 | 1934-02-06 | Process for the preparation of 1-tropic acid-2,2-dimethyl-3-dimethylaminopropanol ester. |
CH179698D CH179698A (en) | 1932-03-22 | 1934-02-06 | Process for the preparation of mandelic acid-2,2-dimethyl-3-diethylaminopropanol ester. |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH179696D CH179696A (en) | 1932-03-22 | 1934-02-06 | Process for the preparation of d-tropic acid-2,2-dimethyl-3-diethylaminopropanol ester. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH179698D CH179698A (en) | 1932-03-22 | 1934-02-06 | Process for the preparation of mandelic acid-2,2-dimethyl-3-diethylaminopropanol ester. |
Country Status (1)
Country | Link |
---|---|
CH (3) | CH179696A (en) |
-
1934
- 1934-02-06 CH CH179696D patent/CH179696A/en unknown
- 1934-02-06 CH CH179697D patent/CH179697A/en unknown
- 1934-02-06 CH CH179698D patent/CH179698A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH179698A (en) | 1935-09-15 |
CH179696A (en) | 1935-09-15 |
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