CH155047A - Process for the preparation of 3-dimethylamino-2-dimethyl-1-benzoyloxypropane. - Google Patents
Process for the preparation of 3-dimethylamino-2-dimethyl-1-benzoyloxypropane.Info
- Publication number
- CH155047A CH155047A CH155047DA CH155047A CH 155047 A CH155047 A CH 155047A CH 155047D A CH155047D A CH 155047DA CH 155047 A CH155047 A CH 155047A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethylamino
- dimethyl
- benzoyloxypropane
- preparation
- salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000003444 anaesthetic Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Description
Verfahren zur Herstellung von 3-Dimethylamino-2-dimethyl-l-benzoylogypropan. Es wurde gefunden, dass -die aromatischen Ester der Aminoalkohole von der Formel
EMI0001.0005
(wobei R Alkyl, R' Wasserstoff oder Alkyl bedeutet), als Mittel zur örtlichen Schmerz betäubung besonders günstige Eigenschaften zeigen.
Die als Augangs;s:toffe dienenden Al koholbasen entstehen aus Aldehydbasen, wel che durch Kondensation von Aldehyden der allgemeinen Formel Rt>CHCHO mit Form aldehyd und primären oder sekundären aliphatischen Aminen erhalten werden, durch Reduktion zum Beispiel mit Natriumamal- gam in schwach essigsaurer Lösung.
Bei der Einwirkung von aromatischen Säuren oder Derivaten, vorzugsweise von Säurechloriden, auf die Alkoholbasen entstehen glatt und mit guter Ausbeute die Ester, welche gut kristallisierte, auch in heissem Wasser be ständig Hydrochloride bilden.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von 3-Di- methylamino - 2 - dimethyl -1- benzoyloxypro- pan, welches dadurch gekennzeichnet ist, dass man auf 3-Dimethylamino-2-dimethyl-pro- pan-l-ol Benzoylchlorid einwirken lässt.
Das 3-Dimethylamino-2-dimethyl-l-ben- zoyloxypropan bildet mit Säuren in Wasser leicht lösliche Salze. Das in farblosen, silber glänzenden Blättchen kristallisierende Hydro- chlorid schmilzt bei 153 .
Die neue Verbindung soll in Form ihrer Salze der anästhesierenden Wirkungen wegen in der Heilkunde Verwendung finden. <I>Beispiel:</I> 5,5 Teile 3-Dimethylamino-2-dimethyl- propan-l-ol (Siedepunkt 166 bis 168 bei 760 mm) werden in 6 Teilen Chloroform ge löst und unter Kühlung mit einer Lösung von 6 Teilen Benzoylehloricl in wenig Chloroform versetzt. Man erwärmt sodann eine Stunde auf 40' und fällt mit rlther. Das ausfallende Hydrochlorid wird aus Isopropylalkohol um kristallisiert und schmilzt bei 153 .
Process for the preparation of 3-dimethylamino-2-dimethyl-1-benzoylogypropane. It has been found that the aromatic esters of the amino alcohols of the formula
EMI0001.0005
(where R is alkyl, R 'is hydrogen or alkyl), show particularly favorable properties as an agent for local pain relief.
The alcohol bases used as starting materials arise from aldehyde bases, which are obtained by condensation of aldehydes of the general formula Rt> CHCHO with form aldehyde and primary or secondary aliphatic amines, for example by reduction with sodium amalgam in weakly acetic acid solution .
When aromatic acids or derivatives, preferably acid chlorides, act on the alcohol bases, the esters are formed smoothly and with good yield, which crystallize well and constantly form hydrochlorides even in hot water.
The present invention relates to a process for the preparation of 3-dimethylamino-2-dimethyl-1-benzoyloxypropane, which is characterized in that benzoyl chloride is used on 3-dimethylamino-2-dimethyl-propan-1-ol can act.
The 3-dimethylamino-2-dimethyl-1-benzoyloxypropane forms easily soluble salts with acids in water. The hydrochloride, which crystallizes in colorless, shiny silver flakes, melts at 153.
The new compound should be used in medicine in the form of its salts because of its anesthetic effects. <I> Example: </I> 5.5 parts of 3-dimethylamino-2-dimethyl-propan-l-ol (boiling point 166 to 168 at 760 mm) are dissolved in 6 parts of chloroform and, with cooling, with a solution of 6 Parts of Benzoylehloricl in a little chloroform are added. The mixture is then warmed to 40 'for one hour and precipitated with ether. The precipitated hydrochloride is crystallized from isopropyl alcohol and melts at 153.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE155047X | 1929-11-01 | ||
| CH153040T | 1930-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH155047A true CH155047A (en) | 1932-05-31 |
Family
ID=25716121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155047D CH155047A (en) | 1929-11-01 | 1930-09-10 | Process for the preparation of 3-dimethylamino-2-dimethyl-1-benzoyloxypropane. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH155047A (en) |
-
1930
- 1930-09-10 CH CH155047D patent/CH155047A/en unknown
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