CH330125A - Process for the preparation of quinuclidine-2-carboxylic acid - Google Patents
Process for the preparation of quinuclidine-2-carboxylic acidInfo
- Publication number
- CH330125A CH330125A CH330125DA CH330125A CH 330125 A CH330125 A CH 330125A CH 330125D A CH330125D A CH 330125DA CH 330125 A CH330125 A CH 330125A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- quinuclidine
- preparation
- acid
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- LIUAALCHBQSCCX-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane-2-carboxylate Chemical compound C1CN2C(C(=O)O)CC1CC2 LIUAALCHBQSCCX-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Chinuclidin-2-carbonsäure Die Cliinuclidin-\?-earbonsäure ist bekannt. Die bekannten Methoden zu deren Herstel lung sind jedoch kompliziert und mühsam.
Die vorliegende Erfindung bezieht. sieh auf ein neues Verfahren zur Herstellung der Chinuelidin-2-carbonsäure und ist dadurch ge kennzeichnet, dass man a-Halogen-ss-piperidyl- (4)-propionsäure oder ihre Salze mit säure bindenden Mitteln erhitzt; aus dem so erhal tenen Salz der Chinitclidin-2-carbonsäiire kann.. man nach an sich bekannten Methoden die Säure freisetzen. Eine bevorzugte Ausfüh i ungsform des neuen Verfahrens besteht darin, dass man a-Chlor-ss-piperidyl-(4)-pro- pionsäure mit überschüssigem Alkalihydroxyd in wässriger Lösung erhitzt..
Das neue Verfahren ergibt gute Ausbeu ten. Die Ausgangsstoffe sind leicht zugänglich. Die Chinuclidin-2-carbonsäure kann als Zwischenprodukt zur Herstellung von Desin fektionsmitteln, Textilhilfsstoffen und von Heilmitteln verwendet werden.
Die Erfindung wird im nachstehenden Bei spiel beschrieben. Zwischen Gewichtsteilen und VOlllmtellen besteht. die gleiche Beziehung wie zwischen g und cm3. Die Temperaturen sind in Celsiusgraden angegeben. Die Schmelz punkte sind im hapillarrohr bestimmt. und urkorrigiert.
<I>Beispiel</I> 0,9 Gewichtsteile Hydrochlorid von a- Chloi--ss-piperidyl-(4)-propionsäure werden mit 8 Volumteilen ln-Natriumhydroxydlösung während 2 Stunden am Rückfluss gekocht. Schon nach etwa 30 Minuten reagiert die Lösung nicht. mehr phenolphthaleinalkaliseh. Die abgekühlte Lösung wird mit Salzsäure kongosauer gestellt und bei vermindertem Druck eingedampft. Der Trockenrückstand wird mit absolutem Äthanol erschöpfend ex trahiert. Beim Einengen scheiden sich allmäh lich 0,63 Gewichtsteile farblose Kristalle aus.
Durch Umkristallisieren aus Äthanol können diese ganz rein erhalten werden. Sie schmel zen bei 290-291 unter Zersetzung und stel len das Hydrochlorid der Chinttelidin-2-car- bonsäure dar.
Die freie Cliinuclidin-2-carbonsäure ent steht daraus nach üblichen Methoden, bei spielsweise durch Behandlung mit. Silberoxyd. Sie schmilzt bei 275-27811 unter Zersetzung.
Das Hydrobromid kann aus Äthanol um kristallisiert werden und schmilzt bei 277 bis 278 unter Zersetzung.
Das als Ausgangsstoff verwendete Hydro- chlorid der a-Chlor-ss-piperidyl-(4)-propion- säure kann auf folgende Art erhalten werden 40 Gewichtsteile a-Chlor-ss-N-benzoyl-pi- peridyl-(4)-propionsäure (vgl. Harris and Work, Biochem. J. 46, 190 [1950]) werden mit 250 Volumteilen konzentrierter Salzsäure und 200 Volumteilen Wasser unter Rückfluss gekocht.
Die abgekühlte Mischung wird mit Chloroform extrahiert; aus der wä.ssrigen Lö sung erhält man beim Eindampfen im Va kuum und Anreiben mit Aceton das neue Hydrochlorid, welches durch Umkristallisie- ren aus Methanol-Aceton gereinigt werden kann. Es schmilzt bei 177-183 .
Process for the preparation of quinuclidine-2-carboxylic acid Cliinuclidine-2-carboxylic acid is known. The known methods for their produc- tion, however, are complicated and laborious.
The present invention relates. see a new process for the preparation of quinuelidine-2-carboxylic acid and is characterized in that a-halo-ss-piperidyl- (4) -propionic acid or its salts are heated with acid-binding agents; the acid can be released from the quinitclidine-2-carboxylic acid salt obtained in this way by methods known per se. A preferred embodiment of the new process consists in heating a-chloro-ß-piperidyl- (4) -propionic acid with excess alkali metal hydroxide in an aqueous solution.
The new process gives good yields. The starting materials are easily accessible. The quinuclidine-2-carboxylic acid can be used as an intermediate in the production of disinfectants, textile auxiliaries and medicinal products.
The invention is described in the following example. There is between parts by weight and full parts. the same relationship as between g and cm3. The temperatures are given in degrees Celsius. The melting points are determined in the hapillary tube. and corrected.
<I> Example </I> 0.9 parts by weight of the hydrochloride of α-chloro-β-piperidyl- (4) -propionic acid are refluxed with 8 parts by volume of ln sodium hydroxide solution for 2 hours. The solution does not react after about 30 minutes. more phenolphthalein alkaline. The cooled solution is made acidic to the Congo with hydrochloric acid and evaporated under reduced pressure. The dry residue is extracted exhaustively with absolute ethanol. On concentration, 0.63 parts by weight of colorless crystals gradually separate out.
These can be obtained completely pure by recrystallization from ethanol. They melt at 290-291 with decomposition and represent the hydrochloride of chinttelidin-2-carboxylic acid.
The free Cliinuclidin-2-carboxylic acid ent is therefrom by customary methods, for example by treatment with. Silver oxide. It melts at 275-27811 with decomposition.
The hydrobromide can be crystallized from ethanol and melts at 277 to 278 with decomposition.
The hydrochloride of α-chloro-ß-piperidyl- (4) -propionic acid used as starting material can be obtained in the following manner: 40 parts by weight of α-chloro-ß-N-benzoyl-piperidyl- (4) -propionic acid (cf. Harris and Work, Biochem. J. 46, 190 [1950]) are refluxed with 250 parts by volume of concentrated hydrochloric acid and 200 parts by volume of water.
The cooled mixture is extracted with chloroform; From the aqueous solution, by evaporation in a vacuum and rubbing with acetone, the new hydrochloride is obtained, which can be purified by recrystallization from methanol-acetone. It melts at 177-183.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH330125T | 1954-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH330125A true CH330125A (en) | 1958-05-31 |
Family
ID=4501584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH330125D CH330125A (en) | 1954-11-30 | 1954-11-30 | Process for the preparation of quinuclidine-2-carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH330125A (en) |
-
1954
- 1954-11-30 CH CH330125D patent/CH330125A/en unknown
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