CH297704A - Process for the production of a new basic ether. - Google Patents
Process for the production of a new basic ether.Info
- Publication number
- CH297704A CH297704A CH297704DA CH297704A CH 297704 A CH297704 A CH 297704A CH 297704D A CH297704D A CH 297704DA CH 297704 A CH297704 A CH 297704A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- new basic
- dependent
- radical
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 11
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- -1 Arylsulfonyloxy radicals Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen basischen Äthers. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Basisehen Äthers, nämlich des 1-(o-0xy-phen- oxy)-\?-isopropylamino-propans. Es soll als Pharmazeutikum, vor allem aber als Zwi schenprodukt zur Herstellung weiterer Deri- @-ate Verwendung finden.
Das den Gegenstand des Patentes bildende Verfahren ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI0001.0010
mit einer Verbindung der Formel
EMI0001.0011
umsetzt, worin X und Y reaktionsfähige, mit Ausnahme einer in einem von ihnen enthal tenen -NH-C,'rruppe sich bei der Reaktion ab spaltende Reste sind, wie z. B. ein Halogen atom, ein Alkyl- resp. Ary1sulfonyloxy-Radi- kal.
Man kann erfindungsgemäss beispielsweise 1-(o-0xy--phenoxy) 2-amino-propan mit einem Isopropylhalogenid umsetzen. Vorzugsweise arbeitet man dabei in einem Lösungsmittel, wie z. B. Benzol, Toluol, Xylol usw.
Ferner kann man erfindungsgemäss auch so verfahren, dass man 1-(o-Oxy-phenoxy)-2- lialogen-propan mit Isopropylamin umsetzt. Bei beiden Ausführungsvarianten kann man in Anwesenheit. eines Kondensations- resp. säurebindenden Mittels arbeiten. Hierzu kann ein tertiäres Amin, wie z.
B. Triäthyl- a.min oder das als Ausgangsmaterial ange wandte Amin, sofern es im Überschuss zuge setzt wird, dienen; ferner können Alkalien, z. B. Alkaliamide, Alkalilaugen, Salze schwa cher Säuren mit Alkalien usw., als Konden sationsmittel verwendet werden.
Das so erhaltene 1-(o-Oxy-phenoxy)-2-iso- propylamino-propan siedet unter 12 mm bei 126-128 C.
Das Chlorhydrat der Verbindung schmilzt bei 128-129 C.
Der neue basische Äther soll als Zwischen produkt und als Pharmazeutikum Verwen dung finden.
<I>Beispiel, 1:</I> 20 g 1-(o-Oxy-phenoxy)-2-chlor-propan werden mit 100 em3 einer benzolischen Lö sung von 33,5 g Isopropylamin unter Zusatz von 17 em3 Triäthylamin 15 Stunden in einem geschlossenen Gefäss auf 170 C erhitzt.
Nach dem Abkühlen versetzt man die Re aktionsmasse mit Wasser, trennt die Benzol- schiebt ab und extrahiert mit verdünnter Salzsäure die basischen Anteile heraus. Die saure wässerige Lösung wird alkalisch ge macht, das sieh abscheidende Öl in Äther auf genommen. Die Ätherlösung wird getrocknet und verdampft und der Rückstand im Va kuum destilliert. Das so in befriedigender Ausbeute erhal tene 1-(o-Oxy-phenoxy) 2-isopropylamino-pro- pan siedet unter 12 mm bei 126-128 C. Das Chlorhydrat schmilzt bei 128-129 C und bil det weisse, gut wasserlösliche Kristalle.
<I>Beispiel</I> 25 Teile 1-(o-Oxy-phenoxy) 2-aminopropan in 150 em3 Benzol werden mit der berechne ten Menge Isopropylbromid und Triäthyl- amin in einem geschlossenen Gefäss auf 150 C erhitzt. Man arbeitet wie im Beispiel 1 an gegeben auf und erhält das 1-(o-Oxy-phen- oxy )-2-isopropyl-amino-propan in befriedigen der Ausbeute und guter Reinheit.
Process for the production of a new basic ether. The subject of the present patent is a process for the production of a new basic ether, namely 1- (o-oxy-phenoxy) - \? - isopropylamino-propane. It should be used as a pharmaceutical, but above all as an intermediate product for the production of further Deri- @ -ate.
The method forming the subject of the patent is characterized in that a compound of the formula
EMI0001.0010
with a compound of the formula
EMI0001.0011
converts, wherein X and Y are reactive, with the exception of one contained in one of them -NH-C, 'rruppe in the reaction from cleaving radicals, such as. B. a halogen atom, an alkyl, respectively. Arylsulfonyloxy radicals.
According to the invention, for example 1- (o-oxy-phenoxy) 2-aminopropane can be reacted with an isopropyl halide. It is preferable to work in a solvent, such as. B. benzene, toluene, xylene, etc.
Furthermore, according to the invention, one can proceed in such a way that 1- (o-oxy-phenoxy) -2-lialogenopropane is reacted with isopropylamine. With both variants you can be present. a condensation resp. acid binding agent work. For this purpose, a tertiary amine, such as.
B. triethyl a.min or the amine used as starting material, if it is added in excess, serve; furthermore, alkalis, e.g. B. alkali amides, alkali solutions, salts of weak acids with alkalis, etc., are used as condensation agents.
The 1- (o-oxy-phenoxy) -2-isopropylamino-propane obtained in this way boils below 12 mm at 126-128 C.
The hydrochloride of the compound melts at 128-129 C.
The new basic ether is to be used as an intermediate product and as a pharmaceutical.
<I> Example, 1: </I> 20 g of 1- (o-oxy-phenoxy) -2-chloropropane are mixed with 100 em3 of a benzene solution of 33.5 g of isopropylamine with the addition of 17 em3 of triethylamine for 15 hours heated to 170 ° C in a closed vessel.
After cooling, water is added to the reaction mixture, the benzene is separated off and the basic components are extracted with dilute hydrochloric acid. The acidic aqueous solution is made alkaline, and the oil which separates out is absorbed in ether. The ether solution is dried and evaporated and the residue is distilled in vacuo. The 1- (o-oxy-phenoxy) 2-isopropylamino-propane obtained in this way in a satisfactory yield boils below 12 mm at 126-128 ° C. The chlorohydrate melts at 128-129 ° C. and forms white, readily water-soluble crystals.
<I> Example </I> 25 parts of 1- (o-oxy-phenoxy) 2-aminopropane in 150 cubic meters of benzene are heated to 150 C in a closed vessel with the calculated amount of isopropyl bromide and triethylamine. The procedure is as given in Example 1 and the 1- (o-oxy-phenoxy) -2-isopropylamino-propane is obtained in satisfactory yield and good purity.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH297704T | 1950-09-16 | ||
| CH293813T | 1950-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH297704A true CH297704A (en) | 1954-03-31 |
Family
ID=25733439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH297704D CH297704A (en) | 1950-09-16 | 1950-09-16 | Process for the production of a new basic ether. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH297704A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275629A (en) * | 1963-03-20 | 1966-09-27 | Monsanto Co | Substituted aryloxyalkylene amines |
-
1950
- 1950-09-16 CH CH297704D patent/CH297704A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275629A (en) * | 1963-03-20 | 1966-09-27 | Monsanto Co | Substituted aryloxyalkylene amines |
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