DE1543900C3 - N-Phenyl-N- (3-alkoxy-2-hydroxy) propylamines and processes for their preparation, as well as medicaments containing these compounds - Google Patents
N-Phenyl-N- (3-alkoxy-2-hydroxy) propylamines and processes for their preparation, as well as medicaments containing these compoundsInfo
- Publication number
- DE1543900C3 DE1543900C3 DE19661543900 DE1543900A DE1543900C3 DE 1543900 C3 DE1543900 C3 DE 1543900C3 DE 19661543900 DE19661543900 DE 19661543900 DE 1543900 A DE1543900 A DE 1543900A DE 1543900 C3 DE1543900 C3 DE 1543900C3
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- phenyl
- compounds
- propylamines
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000006308 propyl amino group Chemical class 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N Diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001989 choleretic Effects 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003142 primary aromatic amines Chemical class 0.000 description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N Allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 alkyl radical Chemical group 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000731 choleretic agent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
in der R einen Alkylrest mit 1 bis 4 Kohlenstoffatomen oder den Allylrest, X Wasserstoff, die Methylgruppe oder die Methoxygruppe und Y Wasserstoff oder ein Chloratom bedeutet.in which R is an alkyl radical having 1 to 4 carbon atoms or the allyl radical, X is hydrogen, the Methyl group or the methoxy group and Y denotes hydrogen or a chlorine atom.
2. Verfahren zur Herstellung der Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß man in an sich bekannter Weise primäre aromatische Amine der allgemeinen Formel2. Process for the preparation of the compounds according to claim 1, characterized in that primary aromatic amines of the general formula are used in a manner known per se
2020th
mit einem Glycidyläther der allgemeinen Formel with a glycidyl ether of the general formula
CH2-CH 2 -
CH-CH2ORCH-CH 2 OR
umsetzt und in üblicher Weise aufarbeitet.implements and processed in the usual way.
3. Arzneimittel, enthaltend Verbindungen nach Anspruch 1 als choleretischen Wirkstoff.3. Medicaments containing compounds according to claim 1 as a choleretic active ingredient.
Die Gegenstände der Erfindung sind den Patentansprüchen zu entnehmen.
Als besonders vorteilhaft für die Durchführung des erfindungsgemäßen Verfahrens hat sich die Verwendung
von niedrigen Alkoholen, vorzugsweise von 96%igem Äthylalkohol als Lösungsmittel erwiesen.
Es wurde weiterhin festgestellt, daß bei Anwendung eines Überschusses an primärem aromatischem Amin,
vorzugsweise im Molverhältnis 2:1, zum entsprechenden
Glycidyläther, die Ausbeuten an den Verfahrensprodukten zwischen 73 und 93% betragen,
während bei äquimolaren Ansätzen die Ausbeuten jeweils nur um 50% liegen. Aus dem nach Abdampfen
des Lösungsmittels verbleibenden Reaktionsgemisch läßt sich bei der fraktionierten Destillation unter vermindertem
Druck das nicht umgesetzte primäre Amin in allen Fällen zu mindestens 90% zurückgewinnen.
The subject matter of the invention can be found in the claims.
The use of lower alcohols, preferably 96% ethyl alcohol, as solvents has proven to be particularly advantageous for carrying out the process according to the invention. It was also found that when using an excess of primary aromatic amine, preferably in a molar ratio of 2: 1, to the corresponding glycidyl ether, the yields of the process products are between 73 and 93%, while with equimolar batches the yields are only around 50% . In all cases, at least 90% of the unreacted primary amine can be recovered from the reaction mixture remaining after the solvent has been evaporated off in the fractional distillation under reduced pressure.
Die erfindungsgemäß herstellbaren Verbindungen zeigen bei geringer Toxizität eine überraschend gute choleretische Wirkung.The compounds which can be prepared according to the invention show surprisingly good toxicity with low toxicity choleretic effect.
Das erfindungsgemäße Verfahren soll durch folgende Beispiele näher erläutert werden.The process according to the invention is to be explained in more detail by the following examples.
N-(4'-Methoxyphenyl)-N-(3-methoxy-2-hydroxy)-propylamin N- (4'-methoxyphenyl) -N- (3-methoxy-2-hydroxy) propylamine
24,6 g 4'-Methoxyphenylamin werden in 50 ecm 96%igem Äthylalkohol gelöst, mit 8,8 g Methyl-· glycidyläther versetzt und 5 Stunden unter Rückfluß gekocht. Das nach dem Abdestillieren des Lösungsmittels im Wasserstrahlvakuum verbliebene öl wird fraktioniert destilliert.24.6 g of 4'-methoxyphenylamine are dissolved in 50 ecm of 96% ethyl alcohol, with 8.8 g of methyl added glycidyl ether and refluxed for 5 hours. That after distilling off the solvent Any oil remaining in a water jet vacuum is fractionally distilled.
Beim Kp. 0,8 mm 82 bis 85° C gehen 11,7g nicht umgesetztes 4'-Methoxyphenylamin.(Fp. 580C) über, beim Kp. 0,4 mm 155 bis 157° C 16,7 g eines farblosen Öls, entsprechend 79% der Theorie.When Kp. 0.8 mm 82 to 85 ° C go 11.7 g of unreacted 4'-methoxy-phenylamine. (Mp. 58 0 C), when Kp. 0.4 mm 155 to 157 ° C 16.7 g of a colorless Oil, corresponding to 79% of theory.
Weitere nach Beispiel 1 herstellbare Verfahrensprodukte sind in der Tabelle zusammengefaßt. Als Lösungsmittel wird 96%iger Äthylalkohol verwendet. Das Verhältnis Amin zu Glycidyläther beträgt 2:1.Further process products which can be prepared according to Example 1 are summarized in the table. When The solvent used is 96% ethyl alcohol. The amine to glycidyl ether ratio is 2: 1.
Die Menge des zurückgewonnenen, nicht umgesetzten Amins beträgt in allen Fällen mindestens 90% der Theorie.The amount of recovered, unreacted amine is at least 90% in all cases Theory.
") Aus Ligroin.
*) Aus Petroläther 40 bis 60".
') Aus Tetrachlorkohlenstoff.
') Aus Essigester.") From ligroin.
*) From petroleum ether 40 to 60 ".
') Made of carbon tetrachloride.
') From ethyl acetate.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC038717 | 1966-03-22 | ||
| DESC038717 | 1966-03-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1543900A1 DE1543900A1 (en) | 1970-01-29 |
| DE1543900B2 DE1543900B2 (en) | 1975-06-05 |
| DE1543900C3 true DE1543900C3 (en) | 1976-03-04 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2907869A1 (en) | PROCESS FOR PREPARING ALIPHATIC AMINES | |
| DE2502247A1 (en) | METHOD FOR PRODUCING N-(TERT. AMINOALKYL)ACRYLAMIDES | |
| DE1214674B (en) | Process for the production of guanidine derivatives | |
| DE1543793A1 (en) | Process for the production of methylpentamethylenediamine | |
| DE1543900C3 (en) | N-Phenyl-N- (3-alkoxy-2-hydroxy) propylamines and processes for their preparation, as well as medicaments containing these compounds | |
| DE2551055A1 (en) | PROCESS FOR THE PREPARATION OF 1,3- OR 1,4-BIS- (AMINOMETHYL) -CYCLOHEXANE | |
| DE1618985B2 (en) | 4-ACETOXY ALKYLBENZYLIDENMALONIC ACID DINITRILE, THE METHOD OF MANUFACTURING IT AND THE FUNGICIDAL AGENTS CONTAINING IT | |
| DE1543900B2 (en) | N-Phenyl-N- (3-alkoxy-2-hydroxy) propylamines and processes for their preparation, as well as medicaments containing these compounds | |
| DE3128575A1 (en) | "METHOD FOR PRODUCING N, 3-DISUBSTITUTED PROPANAMIDS" | |
| DE1518496A1 (en) | Process for the production of amines | |
| DE2749415C2 (en) | Process for the preparation of amines from formamides | |
| DE1158083B (en) | Process for the preparation of basic substituted phenylacetonitriles | |
| DE2510571C2 (en) | Process for the preparation of unsaturated cyanocarbonyl compounds | |
| DE1618310C3 (en) | ||
| DE1215729B (en) | Process for the production of new bis-alkanolamine derivatives and their salts | |
| DE1272286C2 (en) | Process for the preparation of N-substituted aliphatic thiocarboxamides | |
| EP0587534A1 (en) | Process for the preparation of amines | |
| DE1543885C3 (en) | Process for the preparation of 2-methoxy ^ -amino-S-chlorobenzoic acid methyl ester | |
| DE3200559A1 (en) | METHOD FOR PRODUCING CARBAMATES | |
| DE1445655C3 (en) | Process for the preparation of 3,4,5,6-tetrahydropyridine derivatives containing gamma-aminopropyl groups in the 3-position | |
| DE763489C (en) | Process for the preparation of ª-aminoethyl esters of substituted phenylacetic acids | |
| DE1126383B (en) | Process for the production of locally anesthetically effective amino ethers | |
| DE1543128A1 (en) | Process for the preparation of Diels-Alder adducts of fumaric acid and its functional derivatives and the hydrogenation products of these compounds | |
| EP0001983A1 (en) | Method for isolating or obtaining N,N-dimethylaminoacetonitrile from N,N-dimethylaminoacetonitrile/water mixtures | |
| DE870121C (en) | Process for the production of amines |