CH249052A - Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. - Google Patents
Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid.Info
- Publication number
- CH249052A CH249052A CH249052DA CH249052A CH 249052 A CH249052 A CH 249052A CH 249052D A CH249052D A CH 249052DA CH 249052 A CH249052 A CH 249052A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- carboxylic acid
- aryl
- preparation
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001408 amides Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- OMMROWIAJMZSLF-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclopentane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C(O)=O)CCCC1 OMMROWIAJMZSLF-UHFFFAOYSA-N 0.000 description 1
- 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
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- YKQPMEUETFVVNA-UHFFFAOYSA-N n-(4-methoxyphenyl)cyclopentanecarboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1CCCC1 YKQPMEUETFVVNA-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines basischen Amids einer 1-Aryl-cycloalkyl-l-carbonää e. Gegenstand vorliegenden Patentes isst ein Verfahren zur Darstellung eines baeischen Amids einer 1-Aryl-cycloalkyl-l-carbonsäure. Dass Verfahren ist dadurch gekennzeichnet,
dass man eine Verbindung der Formel
EMI0001.0010
auf eine. Verbindung der Formel
EMI0001.0014
worin X und Y zwei mit Ausnahme einer in einem von ihnen enthaltenen NH-Gruppe bei der Reaktion sich abspaltende Reste be deuten, einwirken lässt.
Man kann beispielsweise 1-(4'-Methoxy- phenyl)-,eyclopenta#n-l-,ca;rbansiäure oder .ein reaktionsfähi@ges Derivat derselben, z.
B. ein Halogenid, Anhydrid oder einen Ester, in An- oder Abwesenheit von Kondensations mitteln und Verteilungsmitteln mit ss-Di- methylamino-äthylamin oder eine Metallver- bndung des 1-(4'-Methoxy-phenyl)-cyclo- pentan-l-carbonsäureamids; mit einem reak tionsfähigen Ester des. ss-Dimethylamino- äthanols umsetzen.
Die erhaltene neue Verbindung, das 1-(4' Methoxy-phenyl)-cyclopentan-l-eari'bonsäure- f-idmethylamino-;äthylamid, ist eine Base vom Siedepunkt 147-148 unter 0,18 mm Druck, ihr Hydrochlorid schmilzt bei 134 bis 136 . Die Verbindung soll therapeutische Verwendung finden.
<I>Beispiel 1:</I> 2'3a8 Teile 1-(4'-Methoxy-ph@enyl)-cyclo- pentan-l-carbonsäurechlorid, gelöst in 200 Teilen absolutem Benzol, wemden zu einer Lösung von 8,8 Teilen ss-Dimethylamino- äthylamin in 100 Teilen absolutem Benzol getropft. Das Gemisch wird 2. Stunden unter Rückfluss vom Sieden erhitzt. Nach Erkalten wird mit Wasser verrührt, getrennt und der Benzollösungdurch Ausschütteln mit ver dünnter Salzsäure die Base völlig entzogen.
Die vereinigten wäe:serigen Lösungen wer den auegeäthert, die Base .mit Pottasche in Freiheit gesetzt und in Äther aufgenommen. Das erhaltene 1-(4'-Methoxy-phenyl)-cyclo pentan-l-oarbonsäure-ss-dimethylamino-äthyl- amidsiedet bei 147-148 unter 0,18 mm Druck.
Etwas bessere Ausbeuten erhält man bei Anwendung eines Überschusses an Diamin, d. h. von 1,2' bie 2 Mol auf 1 Mal Säure- ohlorid.
An Stelle des Säure@chloirids können auch andere Halogenide der 1- (4'- Methoxy - phenyl)-cyelopentaan-l-earbonsäure, die Säure selbst, ihre Ester oder ihr Anhydirid verwen det werden.
<I>Beispiel 2:</I> 21,9 Teile 1-(4'-Methoxy-pihenyl)-cyclo- pent9n-l-earbanoäuTeamid werden mit 10,0 Teilen absolutem Toluol und- 5 Teilen fein pulverisiertem Natriumamid versetzt und so lange unter Rühren erwärmt, bis die Ammo- niakbildung beendet ist.
Nach dem Erkalten werden 10,7 Teile ss-Dimethylamino-äthyl- chlorid in 150 Teilen absolutem Toluol zuge geben, die Mischung einige Zeit bei Zimmer temperatur gerührt und anschliessend 2 Stun den lang auf 90-100 erwärmt. Das erkal tete Reaktionsprodukt wird mit 100, Teilen Wasser versetzt, im Seheidetrichter getrennt und die Toluollösung einige Male mit Was ser gewaschen. Dann werden die basis,
ohen Anteile mit verdünnter Säure extrahiert, die vereinigten sauren Lesungen ailka.Zis,eah ge stellt und aus:geäthert. Die Ätherlösungen ergeben nach dem Troeknen mit Natrium sulfat und Verdampfen ein<B>01</B> vom Siede punkt 147-148 unter 0,18 mm Druck.
Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carbonää e. The subject of the present patent is a process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. The procedure is characterized by
that you can get a compound of the formula
EMI0001.0010
on a. Compound of formula
EMI0001.0014
wherein X and Y are two radicals which are split off in the reaction, with the exception of an NH group contained in one of them, can act.
One can, for example, 1- (4'-methoxyphenyl) -, eyclopenta # n-l-, ca; rbansic acid or .a reactive derivative thereof, z.
B. a halide, anhydride or an ester, in the presence or absence of condensation agents and distribution agents with ss-dimethylamino-ethylamine or a metal compound of 1- (4'-methoxyphenyl) cyclopentane-l -carboxamide; react with a reactive ester of .ss-dimethylaminoethanol.
The new compound obtained, 1- (4'-methoxyphenyl) -cyclopentane-1-eari'bonsäure- f-idmethylamino-; ethylamide, is a base with a boiling point of 147-148 under 0.18 mm pressure, its hydrochloride melts 134 to 136. The compound is intended to find therapeutic use.
<I> Example 1: </I> 2'3a8 parts of 1- (4'-methoxy-ph @ enyl) -cyclopentane-1-carboxylic acid chloride, dissolved in 200 parts of absolute benzene, result in a solution of 8.8 Parts of ß-dimethylamino ethylamine in 100 parts of absolute benzene are added dropwise. The mixture is refluxed for 2 hours. After cooling, the mixture is stirred with water, separated and the base is completely removed from the benzene solution by shaking with dilute hydrochloric acid.
The combined aqueous solutions are etherified, the base is set free with potash and taken up in ether. The 1- (4'-methoxyphenyl) -cyclo-pentane-l-carboxylic acid-ß-dimethylamino-ethyl amide boils at 147-148 under 0.18 mm pressure.
Somewhat better yields are obtained when using an excess of diamine; H. from 1.2 to 2 moles to 1 time acid chloride.
Instead of the acid @ chloiride, other halides of 1- (4'-methoxyphenyl) -cyelopentaan-1-carboxylic acid, the acid itself, its ester or its anhydride can also be used.
<I> Example 2: </I> 21.9 parts of 1- (4'-methoxyphenyl) -cyclopent9n-l-earbanoäuTeamid are mixed with 10.0 parts of absolute toluene and 5 parts of finely powdered sodium amide and so heated for a long time with stirring until the ammonia formation has ended.
After cooling, 10.7 parts of β-dimethylamino-ethyl chloride in 150 parts of absolute toluene are added, the mixture is stirred for some time at room temperature and then heated to 90-100 for 2 hours. 100 parts of water are added to the cold-ended reaction product, the mixture is separated in a separate funnel and the toluene solution is washed a few times with water. Then the base
ohen portions extracted with dilute acid, the combined acidic readings ailka.Zis, eah ge and out: etherified. After drying with sodium sulfate and evaporation, the ether solutions produce a <B> 01 </B> boiling point 147-148 under 0.18 mm pressure.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH242245T | 1944-03-20 | ||
| CH249052T | 1944-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH249052A true CH249052A (en) | 1947-05-31 |
Family
ID=25728680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH249052D CH249052A (en) | 1944-03-20 | 1944-03-20 | Process for the preparation of a basic amide of a 1-aryl-cycloalkyl-1-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH249052A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4448991A (en) * | 1980-01-29 | 1984-05-15 | Hoffmann-La Roche Inc. | Cyclohexene derivatives |
-
1944
- 1944-03-20 CH CH249052D patent/CH249052A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4448991A (en) * | 1980-01-29 | 1984-05-15 | Hoffmann-La Roche Inc. | Cyclohexene derivatives |
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