CH245888A - Process for the preparation of a new imidazoline. - Google Patents
Process for the preparation of a new imidazoline.Info
- Publication number
- CH245888A CH245888A CH245888DA CH245888A CH 245888 A CH245888 A CH 245888A CH 245888D A CH245888D A CH 245888DA CH 245888 A CH245888 A CH 245888A
- Authority
- CH
- Switzerland
- Prior art keywords
- imidazoline
- hydrochloride
- preparation
- salt
- ester
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Description
Verfahren zur Herstellung eines neuen Imidazolins. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Imidazolins, das dadurch gekennzeichnet ist, dass man einen reaktionsfähigen Ester des 2-Oxymethyl-,imidazolins bezw. ein Salz die ses Esters mit N-(2-Methoxy-phenyl)-benzyl- amin umsetzt.
Das so erhaltene 2 - EN - (T- Methoxy- phenyl)-N\-benzyl-aminomethyl] -imidazolin bildet ein Hydrochlorid in Form von farb losen Kristallen, die bei 168 bis 169 schmel zen. Es soll pharmazeutische Verwendung finden oder als Zwischenprodukt zur Herstel lung von Heilmitteln dienen.
Als reaktionsfähiger Ester des 2-Oxy- methyl-imidazoIins wird insbesondere ein solcher mit einer starken anorganischen oder organischen Säure, wie z. B. einer Halogen= Wasserstoffsäure sowie einer Alkyl- oder Arylsulfonsäure, und vorzugsweise in Form eines seiner Salze verwendet. Die Umsetzung kann in An- oder Abwesenheit von Verdün nungsmitteln und/oder Kondensationsmitteln durchgeführt werden.
Beispiel: 15,5 Teile 2 - Chlormethyl - imidazolin- hydrochlorid, 50 Teile N-(2-Methogy-phenyl)- benzylamin und 50 Teile Alkohol werden während einigen Stunden auf 90 bis 105 in einem Ölbad erhitzt. Sodann wird der Alkohol abdestilliert und der Rückstand mit einer wässrigen Lösung von 8,4 Teilen Na triumhicarbonat oder mit@.der entsprechenden Menge Ammoniak verrieben.
Das unver brauchte N-(2-Methoxy-phenyl)-benzylamin wird mit einem Lösungsmittel, wie Äther, Benzol oder Toluol, ausgezogen, die wässrige Schicht mit wenig verdünnter Salzsäure neu tralisiert und zum Sieden erhitzt. Beim Ab kühlen der Lösung fällt das 2-<B><I>EN</I></B> -(2'-Me- thoxy - phenyl)-N-benzyl-aminomethyl] -imid- azoIin-hydrochlorid in Form farbloser Kri stalle vom F. 168 bis 169 aus.
An Stelle von Chlormethyl-imidazolin- hydrochlorid kann man von einem andern reaktionsfähigen Ester des 2-Oxymethyl- imidazolins, wie z. B. vom Bromwasserstoff säure- oder Toluolsulfosäure-ester, ausgehen. Ebenso lässt sich an Stelle des Hydrochlorids ein anderes Salz oder die freie Base ver wenden.
Process for the preparation of a new imidazoline. The subject of the present patent is a process for the preparation of a new imidazoline, which is characterized in that a reactive ester of 2-oxymethyl-, imidazoline, respectively. a salt that reacts this ester with N- (2-methoxyphenyl) benzylamine.
The 2 - EN - (T-methoxyphenyl) -N \ -benzyl-aminomethyl] -imidazoline obtained in this way forms a hydrochloride in the form of colorless crystals which melt at 168 to 169. It is intended to be used in pharmaceuticals or as an intermediate in the manufacture of medicinal products.
As a reactive ester of 2-oxymethyl-imidazoIins in particular one with a strong inorganic or organic acid, such as. B. a halogen = hydrogen acid and an alkyl or aryl sulfonic acid, and preferably used in the form of one of its salts. The reaction can be carried out in the presence or absence of diluents and / or condensing agents.
Example: 15.5 parts of 2-chloromethyl-imidazoline hydrochloride, 50 parts of N- (2-methogyphenyl) -benzylamine and 50 parts of alcohol are heated to 90-105 in an oil bath for a few hours. The alcohol is then distilled off and the residue is triturated with an aqueous solution of 8.4 parts of sodium bicarbonate or with the appropriate amount of ammonia.
The unused N- (2-methoxyphenyl) -benzylamine is extracted with a solvent such as ether, benzene or toluene, the aqueous layer is neutralized with a little dilute hydrochloric acid and heated to the boil. When the solution cools, the 2- (2'-methoxy-phenyl) -N-benzyl-aminomethyl] -imide-azoIine hydrochloride falls in the form colorless crystals from F. 168 to 169.
Instead of chloromethyl imidazoline hydrochloride, you can use another reactive ester of 2-oxymethyl imidazoline, such as. B. from the hydrogen bromide acid or toluenesulfonic acid ester, proceed. Another salt or the free base can also be used instead of the hydrochloride.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH245888T | 1944-03-23 | ||
CH242839T | 1944-03-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH245888A true CH245888A (en) | 1946-11-30 |
Family
ID=25728736
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH245888D CH245888A (en) | 1944-03-23 | 1944-03-23 | Process for the preparation of a new imidazoline. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH245888A (en) |
-
1944
- 1944-03-23 CH CH245888D patent/CH245888A/en unknown
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