CH264193A - Process for making an amine. - Google Patents
Process for making an amine.Info
- Publication number
- CH264193A CH264193A CH264193DA CH264193A CH 264193 A CH264193 A CH 264193A CH 264193D A CH264193D A CH 264193DA CH 264193 A CH264193 A CH 264193A
- Authority
- CH
- Switzerland
- Prior art keywords
- imidazoline
- benzyl
- naphthyl
- amino
- amine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000001412 amines Chemical class 0.000 title claims description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 5
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- 229940073608 benzyl chloride Drugs 0.000 claims description 3
- -1 benzyl halide Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines Amins. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Amins, das dadurch gekennzeichnet ist, dass man ein Monosalz des 2-[Naphthyl-(1')-amino-methyl]- imidazolins mit einem reaktionsfähigen Ester des Benzylalkohols umsetzt.
Als Monosalze des genannten Imidazolins werden besonders solche starker Säuren, wie der Halogenwasser- stoffsäuren, der Schwefelsäure, der Salpeter säure, der Alkyl-, Aralkj-l- oder Ary1sulfon- säuren, verwendet.
Reaktionsfähige Ester des Benzylalkoliols sind zum Beispiel solche der halogenwasser- stoffsäuren, der Alkyl- oder Arylsulfonsäuren.
Die Umsetzung kann in An- oder Ab wesenheit voii Verdünnungsmitteln, wie Al kohol oder Dioxan, durchgeführt werden, wo bei auch in Gegenwart. von Katalysatoren ge arbeitet werden kann.
Das so erhaltene 2-[N=Nalilitliyl-(1')-N- benzyl-ainino-nietliyl]-iniidazolin bildet ein Monohydrochlorid vom Schmelzpunkt 207 bis 2090. Es ist neu und soll therapeutische Ver wendung finden, insbesondere als Antihista- minicuni, oder als Zwischenprodukt zur Her stellung von Heilmitteln dienen.
Beispiel: Eine Lösung von 26,1 Teilen 2-[Naphthyl- (1' ) - methyl ] - imidazolin-mono - hy drochlorid und il Teilen Benzylchlorid in 200 Teilen Al kohol wird während einigen Stunden am Rück flusskühler gekocht.. Sodann wird das Lö sungsmittel abdestilliert, der Rückstand mit Wasser versetzt und reit Natriumbicarbonat neutralisiert.
Nach kurzer Zeit. fällt das 2-[N- Naplithyl- (1') -N -benzyl - amino-methy 1] -imid- azolin-mono-liy-drochloricl aus. Es wird abge- nutseht, und aus Alkohol umkristallisiert, wo nach es bei 207 bis 2090 schmilzt.
Bei dieser Umsetzung kann der Alkohol auch durch ein anderes Lösungsmittel, wie zum Beispiel Butylalkohol oder Dioxan, er setzt werden, oder man kann auch mit einem Überschuss von Benzylchlorid arbeiten.
Durch vorsichtiges Versetzen der wässeri gen Lösung des llonochloi@ids in der Kälte mit: verdünnter Natronlauge und Extrahieren der Base mit Methylenchlorid erhält man das kri stalline \?-[N-Naphthyl-(1')-N-benzyl-aniino- ni etliv 1 ] -imidazoliii.
Process for the preparation of an amine. The subject of the present patent is a process for the preparation of an amine, which is characterized in that a monosalt of 2- [naphthyl- (1 ') -amino-methyl] -imidazoline is reacted with a reactive ester of benzyl alcohol.
The monosalts of the imidazoline mentioned are particularly strong acids such as hydrogen halide acids, sulfuric acid, nitric acid, alkyl, aralkyl or arysulfonic acids.
Reactive esters of benzyl alcohol are, for example, those of hydrogen halide acids, alkyl or aryl sulfonic acids.
The reaction can be carried out in the presence or absence of diluents, such as alcohol or dioxane, and in the presence thereof. of catalysts can be used.
The 2- [N = nalilitliyl- (1 ') - N-benzyl-ainino-nietliyl] -iniidazoline obtained in this way forms a monohydrochloride with a melting point of 207 to 2090. It is new and should find therapeutic use, in particular as an antihistaminicuni, or serve as an intermediate for the manufacture of medicinal products.
Example: A solution of 26.1 parts of 2- [naphthyl- (1 ') - methyl] - imidazoline-mono - hydrochloride and il parts of benzyl chloride in 200 parts of alcohol is boiled for a few hours on the reflux condenser Solvent distilled off, water is added to the residue and sodium bicarbonate is neutralized.
After a short time. the 2- [N-naplithyl- (1 ') -N -benzyl-amino-methy 1] -imid-azoline-mono-li-drochloricl precipitates. It is removed and recrystallized from alcohol, where it melts at 207-2090.
In this reaction, the alcohol can also be replaced by a different solvent, such as, for example, butyl alcohol or dioxane, or it is also possible to work with an excess of benzyl chloride.
Careful addition of the aqueous solution of the llonochloi @ id in the cold with: dilute sodium hydroxide solution and extraction of the base with methylene chloride gives the crystalline \? - [N-naphthyl- (1 ') - N-benzyl-aniino-ni etliv 1] imidazoliii.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH264193T | 1944-03-31 | ||
| CH258585T | 1944-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH264193A true CH264193A (en) | 1949-09-30 |
Family
ID=25730184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264193D CH264193A (en) | 1944-03-31 | 1944-03-31 | Process for making an amine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH264193A (en) |
-
1944
- 1944-03-31 CH CH264193D patent/CH264193A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH264193A (en) | Process for making an amine. | |
| DE955233C (en) | Process for the preparation of pentaerythritol trichlorohydrin | |
| EP0050868B1 (en) | Process for the manufacture of n-tert.-alkylamines and formic-acid esters | |
| DE741156C (en) | Process for the production of succinimide | |
| DE838289C (en) | Process for the preparation of d-ª ‡, ª † -Dioxy-ª ‰, ª ‰ -dimethyl-butyric acid amides | |
| DE953879C (en) | Process for the preparation of pyrone (4) | |
| CH264192A (en) | Process for making an amine. | |
| DE839801C (en) | Process for the production of glutamic acid | |
| CH245893A (en) | Process for the preparation of a new imidazoline. | |
| CH245897A (en) | Process for the preparation of a new imidazoline. | |
| CH245889A (en) | Process for the preparation of a new imidazoline. | |
| CH245894A (en) | Process for the preparation of a new imidazoline. | |
| DE1004191B (en) | Process for the preparation of organic hydroxylamine compounds | |
| CH246579A (en) | Process for the preparation of a new imidazoline. | |
| CH245892A (en) | Process for the preparation of a new imidazoline. | |
| DE1052409B (en) | Process for the preparation of threo-1-phenyl-2-amino-propanediol- (1,3) | |
| CH245899A (en) | Process for the preparation of a new imidazoline. | |
| CH200363A (en) | Process for the preparation of methacrylic acid amide. | |
| CH206632A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH245896A (en) | Process for the preparation of a new imidazoline. | |
| CH245891A (en) | Process for the preparation of a new imidazoline. | |
| CH242839A (en) | Process for the preparation of a new imidazoline. | |
| DE2125449A1 (en) | N phenetyl 5 chlorine 2 methoxybenzamide | |
| CH247927A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH240726A (en) | Process for the preparation of a p-amino-benzenesulfonamide. |