CH161978A - Process for the preparation of 4-butylaminobenzoic acid-B-dimethylaminoethyl ester. - Google Patents
Process for the preparation of 4-butylaminobenzoic acid-B-dimethylaminoethyl ester.Info
- Publication number
- CH161978A CH161978A CH161978DA CH161978A CH 161978 A CH161978 A CH 161978A CH 161978D A CH161978D A CH 161978DA CH 161978 A CH161978 A CH 161978A
- Authority
- CH
- Switzerland
- Prior art keywords
- ester
- acid
- preparation
- dimethylaminoethyl ester
- butylaminobenzoic acid
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- YCCRFDDXAVMSLM-UHFFFAOYSA-N 4-(butylamino)benzoic acid Chemical compound CCCCNC1=CC=C(C(O)=O)C=C1 YCCRFDDXAVMSLM-UHFFFAOYSA-N 0.000 claims description 4
- -1 4-butyl Chemical group 0.000 claims description 2
- 230000003444 anaesthetic effect Effects 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005853 β-dimethylaminoethyl group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 4-Butylaminobenzoesäure-ss-dimethylaminoäthylester. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung des 4, Butylaminobenzoesäure -<B>ss</B> - dimethylamino- äthylesters, welches darin besteht, daB man 4-Butylaminobenzoesäure-,ss-halogenäthylester mit Dimethylamin umsetzt.
Der basische Ester bildet farblose Kri stalle, die bei 43' schmelzen. Er besitzt als solcher oder in Form seiner wasser löslichen Salze (Chlorhydrat, Ogalat ete.) ein sehr starkes Anästhesierungsvermögen. <I>Beispiel:
</I> 4-Butylaminobenzoesäure-ss-chloräthylester wird durch Sättigen eine Lösung von 4-Bu- tylaminobenzoesäure in der zehnfachen Menge Äthylenchlorhydrin mit Salzsäuregas, achtstündiges Erhitzen der Mischung auf dem Wasserbade und darauffolgendes Ab destillieren des Äthylenchlorhydrinüberschus- ses im Vakuum erhalten.
Der ölige Rohester wird gereinigt durch Aufnehmen in Äther, Säure-frei-Waschen mit Natriumkarbonat lösung, Trocknen über Kaliumkarbonat und Abdestillieren des Äthers. Der Ester be sitzt in. gereinigtem Zustande den Schmelz punkt 64 bis 65 .
4-Butylaminobenzoesäure-ss-chloräthylester wird unter Kühlung in einer Benzollösung von etwas mehr als der berechneten Menge von Dimethylamin gelöst; diese Lösung wird im Druckgefäss acht Stunden auf<B>1,00'</B> er hitzt. Nach dem Erkalten wird die Benzol lösung mehrfach mit Wasser ausgeschüttelt, wobei Dimethylaminsalz im Wasser gelöst wird, die Esterbase aber in der Benzolschicht bleibt.
Die Esterbase wird der Benzolschicht durch Ausschütteln mit verdünnter Essig säure entzogen, aus der abgetrennten essig sauren Lösung wird die Base mit Natron lauge ausgefällt, in Äther aufgenommen, über Natriumkarbonat getrocknet. Die äthe rische Lösung gibt beim Fällen mit alkoho lischer Salzsäure bis zur lakmusneutralen Reaktion das 4-Butylaminobenzoesäure ,ss-di- methylaminoäthylestermonohydrochlorid vom h\. P. 147 bis 148 .
Process for the preparation of 4-butylaminobenzoic acid-ss-dimethylaminoethyl ester. The present invention relates to a process for the preparation of 4, butylaminobenzoic acid - ß-dimethylaminoethyl ester, which consists in reacting 4-butylaminobenzoic acid, ß-haloethyl ester with dimethylamine.
The basic ester forms colorless crystals which melt at 43 '. As such or in the form of its water-soluble salts (chlorohydrate, ogalat, etc.) it has a very strong anesthetic ability. <I> example:
</I> 4-Butylaminobenzoic acid-ss-chloroethyl ester is obtained by saturating a solution of 4-butylaminobenzoic acid in ten times the amount of ethylene chlorohydrin with hydrochloric acid gas, heating the mixture for eight hours on the water bath and then distilling off the ethylene chlorohydrin excess in vacuo.
The oily crude ester is purified by being taken up in ether, washing acid-free with sodium carbonate solution, drying over potassium carbonate and distilling off the ether. In the purified state, the ester has a melting point of 64 to 65.
4-Butylaminobenzoic acid-s-chloroethyl ester is dissolved in a benzene solution of slightly more than the calculated amount of dimethylamine with cooling; this solution is heated to <B> 1.00 '</B> in the pressure vessel for eight hours. After cooling, the benzene solution is shaken out several times with water, whereby the dimethylamine salt is dissolved in the water, but the ester base remains in the benzene layer.
The ester base is removed from the benzene layer by shaking with dilute acetic acid, the base is precipitated from the separated acetic acid solution with sodium hydroxide solution, taken up in ether and dried over sodium carbonate. The ethereal solution, when precipitated with alcoholic hydrochloric acid, gives 4-butylaminobenzoic acid, ß-dimethylaminoethyl ester monohydrochloride of the h \, until the reaction is neutral to the lactic acid. P. 147 to 148.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH161978T | 1930-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH161978A true CH161978A (en) | 1933-05-31 |
Family
ID=4415237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH161978D CH161978A (en) | 1930-12-22 | 1930-12-22 | Process for the preparation of 4-butylaminobenzoic acid-B-dimethylaminoethyl ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH161978A (en) |
-
1930
- 1930-12-22 CH CH161978D patent/CH161978A/en unknown
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