DE931471C - Process for the production of new esters of the pyridine and piperidine series - Google Patents
Process for the production of new esters of the pyridine and piperidine seriesInfo
- Publication number
- DE931471C DE931471C DEC6470D DEC0006470D DE931471C DE 931471 C DE931471 C DE 931471C DE C6470 D DEC6470 D DE C6470D DE C0006470 D DEC0006470 D DE C0006470D DE 931471 C DE931471 C DE 931471C
- Authority
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- Germany
- Prior art keywords
- acetonitrile
- phenyl
- pyridine
- pyridyl
- methyl
- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Zierfahren zur Herstellung neuer Ester der Pyridin- und Piperidinreihe Es wurde gefunden, daß man zu neuen Estern der Pyridin- und Piperidinreihe gelangen kann, wenn man Monoaryl-acetonitrile, deren Acetonitrilrest wenigstens i Wasserstoffatom enthält, mit kernhalogenierten Pyridinen oder Piperidinen in Gegenwart von halogenwasserstoffabspaltenden Mitteln umsetzt, in den erhaltenen Verbindungen die Nitrilgruppe in an sich bekannter Weise entweder direkt oder über die H O O C- oder Hz N - O C-Gruppe in eine veresterte Carboxylgruppe umwandelt, gegebenenfalls entstandene Pyridine durch Reduktionsmittel in die entsprechenden Piperidine überführt und bzw. oder gegebenenfalls die so hergestellten Pyridin- oder Piperidinverbindungen mit Allcyl-, Alkenyl- oder Arylalkylhalogeniden oder Dialkylsulfaten oder Arylsulfonsäureestern bzw. mit Formaldehyd und Ameisensäure reagieren läßt. Die zur Umsetzung verwendeten Monoarylacetonitrile können in der Methylengruppe des Acetonitrilrestes einen Substituenten enthalten. Beispielsweise seien erwähnt: Phenyl-acetonitril, Naphthyl-acetonitrile, a-Phenyl-a-alkyl-acetonitrile, wie a-Phenyl-a-methyl-acetonitril, 3-Methoxyphenyl-acetonitril, 3, q.-Dimethoxy-phenyl-acetonitril, 3, q.-Methylendioxy-phenyl-acetonitril. Als kernhalogenierte Pyridine und Piperidine kommen z. B. in Frage: 2-Chlor-pyridin, 4-Chlor-pyridin, i-Methyl-3-chlor-piperidin. Diese können auch weiter substituiert sein. So läßt sich 2-Chlor-5-nitro-pyridin als Ausgangsstoff verwenden. Die Umsetzung wird vorzugsweise in inerten Lösungsmitteln, wie z. B. Äther, Benzol oder Toluol, durchgeführt. Für die Abspaltung des Halogenwasserstoffs werden vorteilhaft Natrium, Kalium, Lithium als solche oder in Form ihrer Amide, Hydride, Alkoholate oder Kohlenwasserstoffverbindungen, wie z. B. Natriumamid, Natriumhydrid, Kaliumtert.-butylat, Kalium-tert.-amylat, Butyl-lithium, Phenyl-natrium oder Phenyl-lithium, verwendet.Decorative processes for the production of new esters of the pyridine and piperidine series It has been found that new esters of the pyridine and piperidine series can be obtained can, if one monoaryl acetonitrile, the acetonitrile radical at least i hydrogen atom contains, with nuclear halogenated pyridines or piperidines in the presence of hydrogen halides Reacts means, the nitrile group in the compounds obtained in per se known Way either directly or via the H O O C or Hz N - O C group into an esterified one Converts carboxyl group, any pyridines formed by reducing agents converted into the corresponding piperidines and / or, if appropriate, those prepared in this way Pyridine or piperidine compounds with alkyl, alkenyl or arylalkyl halides or dialkyl sulfates or aryl sulfonic acid esters or with formaldehyde and formic acid lets react. The monoarylacetonitriles used for the reaction can be used in the Methylene group of the acetonitrile radical contain a substituent. For example may be mentioned: phenyl-acetonitrile, naphthyl-acetonitrile, a-phenyl-a-alkyl-acetonitrile, such as a-phenyl-a-methyl-acetonitrile, 3-methoxyphenyl-acetonitrile, 3, q.-dimethoxyphenyl-acetonitrile, 3, q.-methylenedioxy-phenyl-acetonitrile. As nuclear halogenated pyridines and piperidines come z. B. in question: 2-chloro-pyridine, 4-chloro-pyridine, i-methyl-3-chloro-piperidine. These can also be further substituted. So can 2-chloro-5-nitro-pyridine use as raw material. The reaction is preferably carried out in inert solvents, such as B. ether, benzene or toluene performed. For splitting off the hydrogen halide are beneficial sodium, potassium, lithium as such or in form their amides, hydrides, alcoholates or hydrocarbon compounds, such as. B. Sodium amide, Sodium hydride, potassium tert-butoxide, potassium tert-amylate, butyl lithium, phenyl sodium or phenyllithium is used.
Werden bei dieser Umsetzung Acetonitrile erhalten, die an dem mit der Nitrilgruppe verbundenen Kohlenstoffatom noch ein Wasserstoffatom aufweisen, so kann dieses z. B. durch Umsetzung mit einem Alkylhalogenid, wie Methyl-, Äthyl-oder Diäthylaminoäthylchlorid, in Gegenwart von halogenwasserstoffabspaltenden Mitteln durch einen entsprechenden Alkylrest ersetzt werden.If acetonitriles are obtained in this reaction, the with the carbon atom connected to the nitrile group still have a hydrogen atom, so this z. B. by reaction with an alkyl halide, such as methyl, ethyl or Diethylaminoethyl chloride, in the presence of agents that split off hydrogen halides be replaced by a corresponding alkyl radical.
Die Herstellung der Ester aus den bei der Umsetzung gewonnenen a-Aryl-a-pyridyl-acetonitrilen oder a-Aryl-a-piperidyl-acetonitrilen erfolgt direkt oder über die Säuren oder Amide mit entsprechenden Veresterungsmitteln,wobei auch solche Alkohole bzw. Alkoholderivate zur Anwendung gelangen können, die basische Gruppen enthalten.The preparation of the esters from the α-aryl-α-pyridyl-acetonitriles obtained in the reaction or α-Aryl-α-piperidyl-acetonitrile takes place directly or via the acids or amides with appropriate esterifying agents, including such alcohols or alcohol derivatives can be used that contain basic groups.
Die nach dem Verfahren erhaltenen Pyridylessigsäureester lassen sich durch Einwirkung von solchen Reduktionsmitteln, die für die Hydrierung des Pyridinkerns bekannt sind, in die entsprechenden Piperidinverbindungen überführen.The pyridyl acetic acid esters obtained by the process can be by the action of such reducing agents that are responsible for the hydrogenation of the pyridine nucleus are known to be converted into the corresponding piperidine compounds.
Die weitere Substitution der beim vorliegenden Verfahren gebildeten Pyridine und Piperidine am Ringstickstoff kann in irgendeiner Reaktionsstufe geschehen. - Es lassen sich so durch Umsetzung mit Alkylhalogeniden, Alkenylhalogeniden, Arylsulfonsäureestern, Dialkylsulfaten oder auch Arylalkylhalogeniden die entsprechenden quaternären Verbindungen herstellen. Es ist jedoch ausgehend von am Ringstickstoff nicht substituierten Piperidinen auch möglich, tertiäre Piperidine herzustellen.The further substitution of those formed in the present process Pyridines and piperidines on the ring nitrogen can happen in any reaction stage. - By reacting with alkyl halides, alkenyl halides, aryl sulfonic acid esters, Dialkyl sulfates or arylalkyl halides, the corresponding quaternary compounds produce. However, it is based on piperidines which are not substituted on the ring nitrogen also possible to produce tertiary piperidines.
Nach dem Verfahren hergestellte. Verbindungen besitzen wertvolle physiologische Eigenschaften. Sie zeigen, insbesondere der a-Phenyl-a-piperidyl-(2)-essigsäuremethylester, erregende Wirkungen und können als Heilmittel, z. B. als stimulierende Mittel, oder als Zwischenprodukte zur Herstellung von solchen Verwendung finden. Beispiel Zu einer Lösung von 117 g Phenyl-acetonitril und 113 g 2-Chlorpyridin in 4oo ccm absolutem Toluol werden allmählich unter Rühren und Kühlen 8o g pulverisiertes Natriumamid zugegeben. Hierauf wird langsam auf i io bis i 2o° erhitzt und i Stunde bei dieser Temperatur gehalten. Nach dem Erkalten wird mit Wasser versetzt, die Toluollösung mit verdünnter Salzsäure ausgeschüttelt, und die salzsauren Auszüge werden mit konzentrierter Natronlauge alkalisch gemacht. Dabei scheidet sich eine feste Masse ab, die in Essigester aufgenommen und destilliert wird, wobei a-Phenyl-a-pyridyl-(2)-acetonitril bei 15o bis 155° und o,5 mm Druck übergeht. Aus Essigester umkristallisiert schmilzt es bei 88 bis 89°. Ausbeute 135 g.Manufactured using the process. Compounds have valuable physiological Properties. They show, in particular the a-phenyl-a-piperidyl- (2) -acetic acid methyl ester, excitatory effects and can be used as remedies, e.g. B. as a stimulant, or as intermediates for the production of such use. Example to a solution of 117 g of phenylacetonitrile and 113 g of 2-chloropyridine in 4oo ccm of absolute Toluene gradually become 80 g of powdered sodium amide with stirring and cooling admitted. It is then slowly heated to 10 to 20 ° and for an hour at this point Temperature held. After cooling, water is added, the toluene solution extracted with dilute hydrochloric acid, and the hydrochloric acid extracts are concentrated with Caustic soda made alkaline. A solid mass separates out, which is in ethyl acetate is taken up and distilled, with a-phenyl-a-pyridyl- (2) -acetonitrile at 15o up to 155 ° and 0.5 mm pressure passes. Recrystallized from ethyl acetate, it melts at 88 to 89 °. Yield 135g.
In ähnlicher Weise werden ausgehend von 3-Methoxyphenyl-acetoniiril und 2-Chlorpyridin das a-(3-Methoxyphenyl)-a-pyridyl-(2)-acetonitril vom F. 54 bis 55°, aus 3, 4-Dimethoxy-phenylacetonitril und 2-Chlorpyridin das a-(3, 4-Dimethoxy-phenyl) -a-pyridyl- (2) -acetonitril vom I#' 'P0,2192 bis z95°, aus 3,4-Methylen-dioxy-phenylacetonitril und 2-Chlorpyridin das a-(3, 4-Methylendioxy-phenyl)-a-pyridyl-(2)-acetonitril vom Kpo,15 17o bis 18o°, aus Naphthyl-(i)-acetonitril und 2-Chlorpyridin das a-Naphthyl-(i)-a-pyridyl-(2)-acetonitril vom F. 87°, aus a-Phenyl-a-methylacetonitril und 2-Chlorpyridin das a-Phenyla-methyl-a-pyridyl-(2)-acetonitril vom Kp"2 145 bis 15o°, aus Phenyl-acetonitril und 4-Chlorpyridin das a-Phenyl-a-pyridyl-(4)-acetonitril vom F. 76 bis 77°, aus a-Phenyl-a-äthyl-acetonitril und 4-Chlorpyridin das a-Phenyl-a-äthyl-a-pyridyl-(4)-acetonitril vom Kpll 193°, aus Phenyl-acetonitril und N-Methyl-3-chlorpiperidin das a-Phenyla- [N-methyl-piperidyl-(3) ]-acetonitril vom Kpo,2 14o bis 145° erhalten.In a similar way, starting from 3-methoxyphenyl-acetoniiril and 2-chloropyridine a- (3-methoxyphenyl) -a-pyridyl- (2) -acetonitrile with a melting point of 54 bis 55 °, from 3, 4-dimethoxyphenylacetonitrile and 2-chloropyridine the a- (3, 4-dimethoxyphenyl) -a-pyridyl- (2) -acetonitrile from I # '' P0.2192 to z95 °, from 3,4-methylene-dioxy-phenylacetonitrile and 2-chloropyridine a- (3, 4-methylenedioxy-phenyl) -a-pyridyl- (2) acetonitrile from Kpo, 15 17o to 18o °, a-naphthyl- (i) -a-pyridyl- (2) acetonitrile from naphthyl- (i) -acetonitrile and 2-chloropyridine with a temperature of 87 °, from a-phenyl-a-methylacetonitrile and 2-chloropyridine the a-phenyla-methyl-a-pyridyl- (2) -acetonitrile from bp "2 145 to 150 °, from phenyl-acetonitrile and 4-chloropyridine the a-phenyl-a-pyridyl- (4) -acetonitrile from 76 to 77 °, a-phenyl-a-ethyl-a-pyridyl- (4) acetonitrile from a-phenyl-a-ethyl-acetonitrile and 4-chloropyridine vom Kpll 193 °, from phenyl-acetonitrile and N-methyl-3-chloropiperidine the a-phenyla- [N-methyl-piperidyl- (3)] -acetonitrile obtained from Kpo, 2 14o to 145 °.
Die genannten a-Phenyl-a-alkyl-a-pyridyl-acetonitrile können auch durch Alkylierung der a-Phenyla-pyridyl-acetonitrile mit den entsprechenden Alkylhalogeniden in Gegenwart von Natriumamid erhalten werden.The a-phenyl-a-alkyl-a-pyridyl-acetonitrile mentioned can also by alkylation of the a-phenyla-pyridyl-acetonitrile with the corresponding alkyl halides can be obtained in the presence of sodium amide.
ioo g a-Phenyl-a-pyridyl-(2)-acetonitril werden in 400 ccm konzentrierter Schwefelsäure eingetragen, das Gemisch wird über Nacht bei Zimmertemperatur stehengelassen, auf Eis gegossen und mit Soda alkalisch gemacht. Es scheidet sich dabei das a-Phenyl-a-pyridyl-(2)-acetamid ab, das, aus Essigester umkristallisiert, den F. 13q.° zeigt. Ausbeute 96 g. Mit Dimethylsulfat in Alkohol auf dem Wasserbad entsteht daraus in guter Ausbeute das entsprechende N-Methyl-pyridinium-methosulfat vom F. 1650.100 g of a-phenyl-a-pyridyl- (2) -acetonitrile are concentrated in 400 ccm Sulfuric acid entered, the mixture is left to stand overnight at room temperature, poured on ice and made alkaline with soda. The a-phenyl-a-pyridyl- (2) -acetamide separates from, which, recrystallized from ethyl acetate, shows the F. 13q. °. Yield 96g. With Dimethyl sulfate in alcohol on the water bath is produced from it in good yield Corresponding N-methyl-pyridinium-methosulphate from 1650.
ioo g des erhaltenen a-Phenyl-a-pyridyl-(2)-acetamids, in 1 1 Methylalkohol gelöst und 6 Stunden bei Wasserbadtemperatur mit Chlorwasserstoff behandelt, liefern nach dem Einengen, Verdünnen mit Wasser und Alkalischmachen mit Soda den a-Phenyl-a-pyridyl-(2)-essigsäuremethylester in einer Ausbeute von 9o g, F. 74 bis 75° (aus 5o'o/oigem Alkohol). Bei der Veresterung mit Äthylalkohol erhält man in ähnlicher Weise den entsprechenden a-Phenyl-a-pyridyl- (2) -essigsäureäthylester vom Kpo,4 155 bis 16o°. .100 g of the a-phenyl-a-pyridyl- (2) -acetamide obtained in 1 l of methyl alcohol dissolved and treated with hydrogen chloride for 6 hours at water bath temperature, deliver after concentrating, diluting with water and making alkaline with soda the methyl a-phenyl-a-pyridyl- (2) -acetate in a yield of 90 g, melting point 74 to 75 ° (from 50% alcohol). During the esterification with ethyl alcohol the corresponding a-phenyl-a-pyridyl- (2) ethyl acetate from Kpo, 4155 to 16o °. .
Zu diesen Estern kann man auch gelangen, wenn man statt des Amids direkt das a-Phenyl-a-pyridyl-(2)-aceto@nitril in dem betreffenden Alkohol gelöst, der gleichen Behandlung mit Chlorwasserstoff bei Wasserbadtemperatur unterzieht.These esters can also be obtained if instead of the amide directly the a-phenyl-a-pyridyl- (2) -aceto @ nitrile dissolved in the alcohol in question, subjected to the same treatment with hydrogen chloride at water bath temperature.
Durch Hydrierung von 5o g a-Phenyl-a-pyridyl-(2)-essigsäuremethylester in Eisessig in Gegenwart von i g Platinkatalysator bei Zimmertemperatur erhält man unter Aufnahme von 6 Wasserstoffatomen in theoretischer Ausbeute den a-Phenyla-piperidyl- (2) -essigsäuremethylester vom Kp0,0 135 bis 137°. Das N-Methylderivat, mit Formaldehyd und Ameisensäure dargestellt, siedet beim KPo,4 153°.By hydrogenation of 50 g of a-phenyl-a-pyridyl- (2) -acetic acid methyl ester in glacial acetic acid in the presence of 1 g of platinum catalyst at room temperature is obtained with uptake of 6 hydrogen atoms in theoretical yield the a-phenyla-piperidyl- (2) methyl acetate with a boiling point of 135 ° to 137 °. The N-methyl derivative, with formaldehyde and formic acid, boils at KPo, 4153 °.
Zum a Phenyl-a-piperidyl-(2)-essigsäuremethylester gelangt man auch folgendermaßen: Durch Hydrierung von a-Phenyl-a-pyridyl-(2)-acetamid, ebenfalls mit Platinkatalysator, erhält man das entsprechende a-Phenyl-a-piperidyl-(2)-acetamid, dessen Acetat, aus Essigester umkristallisiert, bei 158° schmilzt. Dieses liefert durch Verseifung mit kochender Salzsäure das a-Phenyl-a-piperidyl-(2)-essigsäure-hydrochlorid vom Zersetzungspunkt 248°. Die Veresterung mit Methylalkohol liefert den obengenannten Ester. Der entsprechende Äthylester bildet ein Hydrochlorid vom F. 173° und ein N-Methylderivat vom Kpo,4 138 bis 1.I0°. Der n-Propylester gibt ein Hydrochlorid vom F. 181° und ein N-Methylderivat vom Kp"3 140'.A phenyl-a-piperidyl- (2) -acetic acid methyl ester is also obtained as follows: By hydrogenation of a-phenyl-a-pyridyl- (2) -acetamide, Likewise with a platinum catalyst, the corresponding a-phenyl-a-piperidyl- (2) -acetamide is obtained, the acetate of which, recrystallized from ethyl acetate, melts at 158 °. This delivers the a-phenyl-a-piperidyl- (2) -acetic acid hydrochloride by saponification with boiling hydrochloric acid from the decomposition point 248 °. Esterification with methyl alcohol gives the above Ester. The corresponding ethyl ester forms a hydrochloride with a temperature of 173 ° and a N-methyl derivative from Kpo, 4 138 to 1.10 °. The n-propyl ester is a hydrochloride with a temperature of 181 ° and an N-methyl derivative with a bp "3 140 '.
Im weiteren seien folgende, in ähnlicher Weise hergestellte Amide und Ester genannt: a.-Phenyl-a-pyridyl-(4)-acetamid, F. 15,I'; z-Phenyl-a-pyridyl-(2)-a-methyl-acetamid, F. 13o°; x-Phenyl-x-pyridyl-(2)-a-äthyl-acetamid, F. 1o8°; a-Phenyl-a-piperidyl-(2)-a-äthyl-acetamid, F. 151 bis 152'; a-Phenyl-a,-pyridyl-(.I)-essigsäuremethylester, Kpo,2 150°; x - Phenyl -a-piperidyl - (_.) -essigsäuremethylester, Kpo.2 145'; a.-Phenyl-a,- [1\T-methyl-piperidyl-(4)] -essigsäuremethylester, F. 63o; a - Pheny 1-a,-pyridyl-(2)-essigsäure-f-diäthy laminoäthylester, Kpo,2 16o bis 163o; a-Phenyl-a-piperidy 1-(2)-essigsäure-f-diäthylaminoäthylester-hydrochlorid, F. 170°.The following are amides prepared in a similar manner and esters called: a.-Phenyl-a-pyridyl- (4) -acetamide, F. 15, I '; z-Phenyl-a-pyridyl- (2) -a-methyl-acetamide, Mp 130 °; x-phenyl-x-pyridyl- (2) -a-ethyl-acetamide, melting point 108 °; a-Phenyl-a-piperidyl- (2) -a-ethyl-acetamide, F. 151 to 152 '; a-Phenyl-a, -pyridyl- (. I) -acetic acid methyl ester, Kpo, 2 150 °; x - Phenyl-a-piperidyl - (_.) -Acetic acid methyl ester, Kpo.2 145 '; a.-Phenyl-a, - [1 \ T-methyl-piperidyl- (4)] methyl acetate, m.p. 63o; a - Pheny 1-a, -pyridyl- (2) -acetic acid-f-diethy laminoethyl ester, Kpo, 2 16o to 163o; a-Phenyl-a-piperidy 1- (2) -acetic acid-f-diethylaminoethyl ester hydrochloride, 170 ° F.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH931471X | 1944-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE931471C true DE931471C (en) | 1955-08-08 |
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ID=4548801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC6470D Expired DE931471C (en) | 1944-01-19 | 1944-09-22 | Process for the production of new esters of the pyridine and piperidine series |
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| Country | Link |
|---|---|
| DE (1) | DE931471C (en) |
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1944
- 1944-09-22 DE DEC6470D patent/DE931471C/en not_active Expired
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