CH320133A - Process for the preparation of a new piperidine compound - Google Patents
Process for the preparation of a new piperidine compoundInfo
- Publication number
- CH320133A CH320133A CH320133DA CH320133A CH 320133 A CH320133 A CH 320133A CH 320133D A CH320133D A CH 320133DA CH 320133 A CH320133 A CH 320133A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- parts
- acid
- piperidine compound
- weight
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/02—Preparation, purification or separation of ammonia
- C01C1/04—Preparation of ammonia by synthesis
- C01C1/0405—Preparation of ammonia by synthesis from N2 and H2 in presence of a catalyst
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung einer neuen Piperidinverbindung Gegenstand der vorliegenden Erfindung ist die Herstellung des 2-Diphenylmethyl- piperidins der Formel
EMI0001.0005
Diese neue Piperidinverbindung besitzt. eine zentralerregende Wirkung und zudem eine deutliche Weekwirkung. Sie kann als zentral erregendes Pharmakon oder als Weckmittel Verwendung finden.
Die Verbindung wird erhalten, wenn man das 2-Diphenylmethy l-pyridin mit hy drieren- den Mitteln behandelt.
Die Hydrierung lässt sieh mit solchen Mit teln durchführen, die für die Hydrierung des Pyridinringes bekannt sind. So hydriert man beispielsweise mit. Wasserstoff in Gegenwart eines Katalysators, vorzugsweise eines Edel- metallkatalysators, wie Platin, ferner in An wesenheit von Nickel oder Kupferehromit. Das 2-Diphenylmet-hyl-pyridin kann dabei auch in. Form seiner Salze verwendet werden.
Je nach. der Arbeitsweise erhält man die neue Verbindung in Form ihrer Base oder ihrer Salze. Aus den Salzen kann in an sieh bekannter Weise die Base gewonnen werden. Von letzterer wiederum lassen sich durch Um- setzurig mit Säuren, die zur Bildung therapeu tisch verwendbarer Salze geeignet sind, Salze gewinnen, wie z.
B. der Halogenwasserstoff säuren, Schwefelsäure, Salpetersäure, Phos phorsäure, Rhodanwasserstoffsäure, Essig säure, Propionsäure, Oxalsäure, Malonsäure, Bernsteinsäure, Äpfelsäure, Met.hansulfon- säure, Ät.hani-snlfonsäure, Oxyäthansulfonsäure, Benzol- oder Toluolsulfonsäure oder von thera peutisch wirksamen Säuren.
Im folgenden Beispiel besteht zwischen Ge- wichtstei.l und Vohunteil die gleiche Beziehung wie zwischen Gramm und Kubikzentimeter. Die Temperaturen sind in Celsiusgraden an gegeben.
<I>Beispiel</I> 36,75 Gewichtsteile 2 - Diphenylmethyl- pyridin, gelöst in 150 Volumteilen Eisessig; werden mit 1 Gewichtsteil Platinoxyd als Kata lysator bei 40-45 in einer Wasserstoff- Atmosphäre so lange geschüttelt, bis kein Wasserstoff mehr aufgenommen wird.
Der Eisessig wird im Vakuum abgedampft., der Rückstand mit konzentrierter Natronlauge alkalisch gestellt und das dabei ausgeschiedene Öl in Äther aufgenommen. Nach dem Waschen und Trocknen des Äther-Extraktes wird das Lösungsmittel verdampft, der Rückstand in wenig absolutem Essigester gelöst und mit einem Überschuss an Chlorwasserstoff, gelöst in Essigerster, versetzt..
Das dabei in grosser Reinheit entstehende Chlorhydrat des 2-Di- p lienylmethyl-piperidin s der Formel
EMI0002.0008
wird; aus Methanol-Essigester umkristallisiert und schmilzt. bei 281-282 (Zers,.).
o Der oben genannte Ausgangsstoff lässt sich wie folgt gewinnen: In einem Rührwerk werden 193 Gewichts teile Diphenylacetonitril mit 60 Gewichtsteilen pulverisiertem Natriumamid in 500 Voliun- teilen absolutem Toluol während 11/2-2 Stun den auf 120-130 erhitzt.
Dann wird der Kol beninhalt .auf 7011 abgel,:ühlt, worauf 238 Ge wichtsteile 2-Bram-pyridin zuggetropft werden. Die exotherme Reaktion wird durch Kühlung so geleitet, da.ss die Temperatur 85 nicht über schreitet. Nach der Zugabe des Brompyridins wird das Reaktionsgemisch noch während Stunden auf 120-130 erhitzt.
Nach dem Abkühlen werden unter Eiskühlung vorsichtig zuerst 50 Valuinteile Methanol, dann 200 Vo- lumteile Wasser zuggetropft und hierauf die basischen Anteile mit 20 o/oiger Salzsäure aus gezogen.
Dieser Säureauszug wird mit 40 11/oiger Natronlauge alka:liseh gestellt, der entstandene kristalline Niederschlag abgenutscht, mit ziel l@rasser gewaschen, auf der Hutsche getrocknet und aus Methanol umkristallisiert. Man erhält so 208 Gewichtsteile des Diphenyl-pyridyl-(2)- acetonitrils vom F. = 117-118 .
'308 (-ie@viehtsteile Diplienyl-pyridl-(2j- :cetonit.ril, 1000 Volumteile Methanol, 22-1 Ge wichtsteile Kaliumhy droxy d und 335 Volum- teile _'4Tasser werden während 10 Stunden im Autokla.ven auf 2l5-225 erhitzt.
Nach dem, Abkühlen wird das überschüssige Methanol abgedampft, der R.iickstand mit -Äther ausge- zogen, der mit Wasser gewaschen und über Natriumsulfat t-,etrocknet. Nacli dein Abdestillieren des Lösungsmittels wird der, Rückstand im Hochvakuum destilliert,
wobei das 2-Diphenylmetlivl-py ridin bei<B>157</B> bis 159 ;0,025 min übergeht; es erstarrt sofort l@rist.allin und schmilzt bei 60-61 .
Process for the preparation of a new piperidine compound The present invention relates to the preparation of 2-diphenylmethylpiperidine of the formula
EMI0001.0005
This new piperidine compound possesses. a central stimulating effect and also a clear week effect. It can be used as a centrally stimulating drug or as a waking agent.
The compound is obtained when the 2-diphenylmethy l-pyridine is treated with hydrogenating agents.
The hydrogenation can be carried out with those means that are known for the hydrogenation of the pyridine ring. This is how you hydrogenate, for example. Hydrogen in the presence of a catalyst, preferably a noble metal catalyst such as platinum, also in the presence of nickel or copper chromite. The 2-diphenylmethyl pyridine can also be used in the form of its salts.
Depending on. The procedure gives the new compound in the form of its base or its salts. The base can be obtained from the salts in a manner known per se. From the latter, in turn, salts can be obtained by reacting with acids that are suitable for the formation of therapeutically usable salts, such as.
B. the hydrohalic acids, sulfuric acid, nitric acid, phosphoric acid, hydro thodanic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, malic acid, met effective acids.
In the following example, there is the same relationship between weight and excess as between grams and cubic centimeters. The temperatures are given in degrees Celsius.
<I> Example </I> 36.75 parts by weight of 2-diphenylmethylpyridine, dissolved in 150 parts by volume of glacial acetic acid; are shaken with 1 part by weight of platinum oxide as a catalyst at 40-45 in a hydrogen atmosphere until no more hydrogen is absorbed.
The glacial acetic acid is evaporated in vacuo, the residue is made alkaline with concentrated sodium hydroxide solution and the oil which separates out is taken up in ether. After the ether extract has been washed and dried, the solvent is evaporated, the residue is dissolved in a little absolute ethyl acetate and an excess of hydrogen chloride dissolved in ethyl acetate is added.
The resulting high purity chlorohydrate of 2-dip lienylmethyl-piperidine s of the formula
EMI0002.0008
becomes; recrystallized from methanol / ethyl acetate and melts. at 281-282 (dec.).
o The above-mentioned starting material can be obtained as follows: 193 parts by weight of diphenylacetonitrile with 60 parts by weight of powdered sodium amide in 500 parts by volume of absolute toluene are heated to 120-130 for 11/2-2 hours in a stirrer.
Then the contents of the flask are poured off to 7011, whereupon 238 parts by weight of 2-bramopyridine are added dropwise. The exothermic reaction is conducted by cooling so that the temperature does not exceed 85. After the addition of the bromopyridine, the reaction mixture is heated to 120-130 for hours.
After cooling, first 50 parts by volume of methanol and then 200 parts by volume of water are carefully added dropwise while cooling with ice, and the basic components are then extracted with 20% hydrochloric acid.
This acid extract is made alkaline with 40 11 / o sodium hydroxide solution, the crystalline precipitate formed is filtered off with suction, washed with water, dried on a hatch and recrystallized from methanol. 208 parts by weight of diphenyl-pyridyl- (2) -acetonitrile with a melting point of 117-118 are obtained.
'308 (-ie @ vächtsteile Diplienyl-pyridl- (2j-: cetonit.ril, 1000 parts by volume of methanol, 22-1 parts by weight of potassium hydroxide and 335 parts by volume of water are placed in the autoclave on 2l5- 225 heated.
After cooling, the excess methanol is evaporated off, the residue is extracted with ether, which is washed with water and dried over sodium sulfate. After distilling off the solvent, the residue is distilled in a high vacuum,
wherein the 2-diphenylmetal-pyridine passes over at 157 to 159; 0.025 min; it immediately freezes l@rist.allin and melts at 60-61.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH320133T | 1953-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH320133A true CH320133A (en) | 1957-03-15 |
Family
ID=4497885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH320133D CH320133A (en) | 1953-07-06 | 1953-07-06 | Process for the preparation of a new piperidine compound |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT190058B (en) |
| BE (1) | BE530124A (en) |
| CH (1) | CH320133A (en) |
| DE (1) | DE1095280B (en) |
| FR (1) | FR1167463A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254090A (en) * | 1960-04-21 | 1966-05-31 | Agfa Ag | Quaternary mono-unsaturated pyridinium salts |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE507597A (en) * | 1950-12-05 | 1953-04-24 | Schering Corp | PROCESS FOR THE PREPARATION OF SUBSTITUTED PIPERIDINES. |
-
1953
- 1953-07-06 CH CH320133D patent/CH320133A/en unknown
-
1954
- 1954-06-21 AT AT190058D patent/AT190058B/en active
- 1954-07-01 DE DEC9591A patent/DE1095280B/en active Pending
- 1954-07-05 BE BE530124A patent/BE530124A/en unknown
- 1954-07-05 FR FR1167463D patent/FR1167463A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1167463A (en) | 1958-11-25 |
| AT190058B (en) | 1957-06-11 |
| BE530124A (en) | 1957-08-30 |
| DE1095280B (en) | 1960-12-22 |
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