CH249041A - Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. - Google Patents
Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.Info
- Publication number
- CH249041A CH249041A CH249041DA CH249041A CH 249041 A CH249041 A CH 249041A CH 249041D A CH249041D A CH 249041DA CH 249041 A CH249041 A CH 249041A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- ester
- cyclopentane
- cycloalkyl
- aryl
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- AGTWMLGJZNNZGK-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)cyclopentane-1-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1(C(O)=O)CCCC1 AGTWMLGJZNNZGK-UHFFFAOYSA-N 0.000 claims description 5
- -1 1- (3 ', 4'-dimethylphenyl) - cyclopentane - 1 - carboxylic acid halide Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FVODWFGNKCRSIU-UHFFFAOYSA-N CC1=C(C)C=C(C2(CCCC2)C(Cl)=O)C=C1 Chemical compound CC1=C(C)C=C(C2(CCCC2)C(Cl)=O)C=C1 FVODWFGNKCRSIU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines basischen Esters einer 1-Aryl-cycloalkyl-l-earbonsäure. Gegenstand vorliegenden Patentes ist ein Verfahren zur Darstellung eines basischen Esters einer 1- Aryl - cycloalkyl -1- carbon- Aure. Das Verfahren ist dadurch gekenn zeichnet, dass man eine Verbindung der Formel
EMI0001.0007
auf eine Verbindung der Formel
EMI0001.0008
worin X und Y zwei mit Ausnahme eines in einem von ihnen enthaltenen Sauerstoff atoms sich bei der Reaktion abspaltende Reste bedeuten,
einwirken lässt.
Die erhaltene neue Verbindung, der Mor- pholinoäthylester, der 1- (3,4'- Dimethyl- phenyl)-cyclopentan-l-carbonsäure, ist eine, Base vom Siedepunkt 162-164 unter 0,05 mm Druck. Ihr Hydrochlorid schmilzt bei 156-l57 . Die Verbindung soll thera peutische Verwendung finden.
Beispiel: 23,6 Teile 1-(3',4' - Dimethyl - phenyl)- cyclopentan -1- carbonsäurechlorid werden unter Rühren zu 13,1 Teilen Morpholino- äthanol gegeben, wobei Erwärmung eintritt. Das Gemisch wird hierauf unter Rühren auf 180 erhitzt, bis eine homogene Schmelze entstanden ist.
Diese wird vorteilhaft noch warm unter Zusatz von wenig verdünnter Salzsäure in Wasser gelöst und die wässrige Lösung einige Male ausgeäthert. Hierauf wird mit konzentriertem Ammoniak die Base freigemacht und in Äther aufgenom men. Nach einmaligem Waschen der ätheri schen Lösung mit Wasser und Trocknen wird das Lösungsmittel abdestilliert und der als Rückstand erhaltene basische Ester durch Destillation im Vakuum gereinigt. Dieser siedet bei 162-164 unter 0,05 mm Druck.
Die Reaktion kann auch in einem Lösungsmittel, wie Benzol, Toluol, Xylol, Chlorbenzol usw., ausgeführt werden. Man erhält in diesem Fall oft bessere Ausbeuten bei Verwendung eines Überschusses an Aminoalkohol.
Statt des Säurechlorids kann man ein anderes Säurehalogenid oder das Anhydrid anwenden oder auch einen Ester der Car- bonsäure; z. B. den 1-(3',4'-Dimethyl-phe- nyl) - cyclopentan-1- carbonsäuremethylester, mit Morpholinoäthanol in Gegenwart von Natriumalkoholat umsetzen, wobei vorteil haft der entstehende Alkohol durch Destil lation aus dem Reaktionsgemisch entfernt wird.
Zum gleichen Endprodukt gelangt man auch, wenn man die 1-(3',4'-Dimethyl-phe- nyl)-cyclopentan-l-carbonsäure mit einem Morpholinoäthyl-halogenid erhitzt oder ein Salz der 1-(3',4'-Dimethyl-phenyl)-cyclopen- tan-l-carbonsäure mit einem reaktionsfähi gen Ester des Morpholinoäthanols oder einem Salz desselben umsetzt.
Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The subject of the present patent is a process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carbon aure. The process is characterized in that a compound of the formula
EMI0001.0007
to a compound of the formula
EMI0001.0008
where X and Y are two radicals, with the exception of an oxygen atom contained in one of them, which are split off during the reaction,
can act.
The new compound obtained, the morpholino ethyl ester, 1- (3,4'-dimethylphenyl) -cyclopentane-1-carboxylic acid, is a base with a boiling point of 162-164 under 0.05 mm pressure. Its hydrochloride melts at 156-157. The connection is intended to find therapeutic use.
Example: 23.6 parts of 1- (3 ', 4' -dimethyl-phenyl) -cyclopentane-1-carboxylic acid chloride are added to 13.1 parts of morpholino-ethanol with stirring, and heating occurs. The mixture is then heated to 180 ° with stirring until a homogeneous melt has formed.
This is advantageously dissolved in water while still warm with the addition of a little dilute hydrochloric acid and the aqueous solution is extracted with ether a few times. The base is then freed with concentrated ammonia and taken up in ether. After washing the ethereal solution once with water and drying, the solvent is distilled off and the basic ester obtained as residue is purified by distillation in vacuo. This boils at 162-164 under 0.05 mm pressure.
The reaction can also be carried out in a solvent such as benzene, toluene, xylene, chlorobenzene, etc. In this case, better yields are often obtained when using an excess of amino alcohol.
Instead of the acid chloride, another acid halide or the anhydride or an ester of carboxylic acid can be used; z. B. the 1- (3 ', 4'-dimethyl-phenyl) - cyclopentane-1-carboxylic acid methyl ester, react with morpholinoethanol in the presence of sodium alcoholate, the alcohol formed being advantageously removed from the reaction mixture by distillation.
The same end product is also obtained if 1- (3 ', 4'-dimethyl-phenyl) -cyclopentane-1-carboxylic acid is heated with a morpholino ethyl halide or a salt of the 1- (3', 4'- Dimethyl-phenyl) -cyclopentane-1-carboxylic acid with a reactive ester of morpholinoethanol or a salt thereof.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH234452T | 1944-03-20 | ||
| CH249041T | 1944-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH249041A true CH249041A (en) | 1947-05-31 |
Family
ID=25727885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH249041D CH249041A (en) | 1944-03-20 | 1944-03-20 | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH249041A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2704284A (en) * | 1952-06-28 | 1955-03-15 | Abbott Lab | Therapeutic compounds |
-
1944
- 1944-03-20 CH CH249041D patent/CH249041A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2704284A (en) * | 1952-06-28 | 1955-03-15 | Abbott Lab | Therapeutic compounds |
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