AT203006B - Process for the preparation of new esters of piperidyl- (2) -phenylcarbinol and their salts - Google Patents
Process for the preparation of new esters of piperidyl- (2) -phenylcarbinol and their saltsInfo
- Publication number
- AT203006B AT203006B AT261858A AT261858A AT203006B AT 203006 B AT203006 B AT 203006B AT 261858 A AT261858 A AT 261858A AT 261858 A AT261858 A AT 261858A AT 203006 B AT203006 B AT 203006B
- Authority
- AT
- Austria
- Prior art keywords
- salts
- piperidyl
- phenylcarbinol
- preparation
- esters
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 13
- 150000003839 salts Chemical class 0.000 title claims description 7
- 229960004217 benzyl alcohol Drugs 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 241000269627 Amphiuma means Species 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 208000000269 Hyperkinesis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical group C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von neuen Estern des Piperidyl-(2)-phenylcarbinols und von deren Salzen
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von neuen Estern des Piperidyl- (2)- phenylcarbinols und von deren Salzen.
Diese Ester entsprechen der allgemeinen Formel :
EMI1.1
in der R Wasserstoff oder eine. Methyl- odr Athylgruppe bedeutet.
Das Piperidyl- (2)-phenylcarbinol :
EMI1.2
bestitzt zwei asymmetrische Kohlenstoffatuome (*) und kann daher in zwei racemischen stereoisomeren For-
EMI1.3
J.beiden Formen besitzen die folgenden Merkmale : A # Base F. = 141 - 142 C (Kapillare) Hydrochlorid F. = 200 - 202 C (Kapillare) fBase F. = 176-178 C Kapillare) (Crook und Mc. Elvain geben. 171-173 C an) Hydrochlorid F. =120 - 1220 C (Kapillare).
Die vorliegende Erfindung betrifft nur die Herstellung von Estern der Form B und von deren Salzen in Form der racemischen Produkte oder ihrer optisch aktiven Isomeren.
Gemäss der Erfindung können die neuen racemischen oder optisch aktiven Ester der Form B durch Hydrierung eines entsprechenden Pyxidiaesters der allgemeinen Formel :
<Desc/Clms Page number 2>
EMI2.1
in der R die oben angegebenen Bedeutungen besitzt, hergestellt werden. Diese Hydrierung kann aufkatalytischem Wege durch Einwirkung von Wasserstoff auf den Pyridinsster, beispielsweise in Gegenwart von Adams-Platin in essigsaurer Lösung erfolgen. Die Umwandlung der so erhaltenen hydrierten Ester in ihre Salze mit Säuren erfolgt in an sich bekannter Weise.
Die erhaltenen racemischen Ester können gegebenenfalls durch direkte optische Spaltung in ihre optisch aktiven Isomeren getrennt werden.
Die neuen Verbindungen besitzen sehr interessante zentralstimulierende Eigenschaften, die sich beim Tier (Ratte) insbesondere duich eine motorische Hyperaktivität und eine Steigerung der psychischen Befähigung, gewisse Teste auszuführen, bemerkbar machen. Die Essigsäureester sind in dieser Hinsicht die aktivstem Die entsprechenden Alkohole sowohl von der Form B als auch von der Form A und die Ester der Form A sind praktisch in therapeutisch anwendbaren Dosen auf diesem Gebiet unwirksam.
Die optisch aktiven Verbindungen besitzen qualitativ analoge Eigenschaften wie die racemischen Produkte. Sie unterscheiden sich Jedoch quantitativ durch die Intensität ihrer Wirksamkeit, die ihnen auf Grund der beträchtlichen Unterschiede ihrer Sekundärwirkungen eine vorteilhaftere Verwendung verleihen kann. Insbesondere ist das linksdrehende l-Acetoxy-l-phenyl-l-piperidyl- (2')-methanhydrochlorid Form B von ausserordentlichem Interesse.
EMI2.2
Man filtriert den Katalysator ab, versetzt mit 5 cm3 einer ätherischen Salzsäurelösung mit einem Gehalt von 160 g/Liter und dampft im Vakuum ein. Den öligen Rückstand nimmt man in 12 cms warmem Methyl- äthylketon auf.
Es fällt ein kristallines, ungefärbtes Produkt aus, das man. absaugt, mit Methyläthylketon und dann mit wasserfreiem Äther wäscht und trocknet.
EMI2.3
-methan. -hydrochlorid,Beispiel 2 : Man verfährt wie in Beispiel 1 angegeben, aber ausgehend vom linksdrehenden 1- Phenyl-l-acetoxy-l-pyridin- (2')-methan und erhält 1-Pheayl-1-actotxy-1-piperidyl-(2')-methan, dessen Hydrochlorid bei 2320 C (Kapillare) schmilzt, [0. α]D20=-60 (c-0, 4% in Chloroform).
EMI2.4
<Desc / Clms Page number 1>
Process for the preparation of new esters of piperidyl- (2) -phenylcarbinol and their salts
The present invention relates to a process for the preparation of new esters of piperidyl- (2) -phenylcarbinol and their salts.
These esters correspond to the general formula:
EMI1.1
in which R is hydrogen or a. Means methyl or ethyl group.
The piperidyl- (2) -phenylcarbinol:
EMI1.2
has two asymmetric carbon atoms (*) and can therefore be converted into two racemic stereoisomeric
EMI1.3
J. Both forms have the following characteristics: A # Base F. = 141 - 142 C (capillary) Hydrochloride F. = 200 - 202 C (capillary) fBase F. = 176-178 C capillary) (Crook and Mc. Elvain give 171-173 C an) hydrochloride F. = 120-1220 C (capillary).
The present invention relates only to the preparation of esters of the form B and their salts in the form of the racemic products or their optically active isomers.
According to the invention, the new racemic or optically active esters of form B can be prepared by hydrogenation of a corresponding pyxidiac ester of the general formula:
<Desc / Clms Page number 2>
EMI2.1
in which R has the meanings given above. This hydrogenation can be carried out catalytically by the action of hydrogen on the pyridine star, for example in the presence of Adams platinum in acetic acid solution. The conversion of the thus obtained hydrogenated esters into their salts with acids takes place in a manner known per se.
The racemic esters obtained can, if appropriate, be separated into their optically active isomers by direct optical resolution.
The new compounds have very interesting central stimulating properties, which in animals (rats) are particularly noticeable in terms of motor hyperactivity and an increase in the psychological ability to carry out certain tests. The acetic acid esters are the most active in this regard. The corresponding alcohols of both Form B and Form A and the esters of Form A are practically ineffective in therapeutically applicable doses in this area.
The optically active compounds have qualitatively similar properties to the racemic products. However, they differ quantitatively by the intensity of their effectiveness, which can give them a more advantageous use due to the considerable differences in their secondary effects. In particular, the levorotatory l-acetoxy-l-phenyl-l-piperidyl (2 ') methane hydrochloride form B is of exceptional interest.
EMI2.2
The catalyst is filtered off, 5 cm3 of an ethereal hydrochloric acid solution with a content of 160 g / liter are added and the mixture is evaporated in vacuo. The oily residue is taken up in 12 cms warm methyl ethyl ketone.
It turns out a crystalline, uncolored product, which one. suctioned off, washed with methyl ethyl ketone and then with anhydrous ether and dried.
EMI2.3
-methane. Hydrochloride, Example 2: The procedure is as given in Example 1, but starting from the levorotatory 1-phenyl-l-acetoxy-l-pyridine- (2 ') methane and 1-pheayl-1-actotxy-1-piperidyl- (2 ') - methane, the hydrochloride of which melts at 2320 C (capillary), [0. α] 20 D = -60 (c-0.4% in chloroform).
EMI2.4
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR203006X | 1957-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT203006B true AT203006B (en) | 1959-04-25 |
Family
ID=8880147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT261858A AT203006B (en) | 1957-08-09 | 1957-09-19 | Process for the preparation of new esters of piperidyl- (2) -phenylcarbinol and their salts |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT203006B (en) |
-
1957
- 1957-09-19 AT AT261858A patent/AT203006B/en active
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