CH320133A - Verfahren zur Herstellung einer neuen Piperidinverbindung - Google Patents
Verfahren zur Herstellung einer neuen PiperidinverbindungInfo
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 piperidine compound Chemical class 0.000 title description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- MMXYNKLYVRNTCK-UHFFFAOYSA-N diphenyl-2-pyridylmethane Chemical compound C1=CC=CC=C1C(C=1N=CC=CC=1)C1=CC=CC=C1 MMXYNKLYVRNTCK-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NAXKFVIRJICPAO-LHNWDKRHSA-N [(1R,3S,4R,6R,7R,9S,10S,12R,13S,15S,16R,18S,19S,21S,22S,24S,25S,27S,28R,30R,31R,33S,34S,36R,37R,39R,40S,42R,44R,46S,48S,50R,52S,54S,56S)-46,48,50,52,54,56-hexakis(hydroxymethyl)-2,8,14,20,26,32,38,43,45,47,49,51,53,55-tetradecaoxa-5,11,17,23,29,35,41-heptathiapentadecacyclo[37.3.2.23,7.29,13.215,19.221,25.227,31.233,37.04,6.010,12.016,18.022,24.028,30.034,36.040,42]hexapentacontan-44-yl]methanol Chemical compound OC[C@H]1O[C@H]2O[C@H]3[C@H](CO)O[C@H](O[C@H]4[C@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@H]6[C@H](CO)O[C@H](O[C@H]7[C@H](CO)O[C@@H](O[C@H]8[C@H](CO)O[C@@H](O[C@@H]1[C@@H]1S[C@@H]21)[C@@H]1S[C@H]81)[C@H]1S[C@@H]71)[C@H]1S[C@H]61)[C@H]1S[C@@H]51)[C@H]1S[C@@H]41)[C@H]1S[C@H]31 NAXKFVIRJICPAO-LHNWDKRHSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- RWTNXJXZVGHMGI-UHFFFAOYSA-N desoxypipradrol Chemical compound N1CCCCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 RWTNXJXZVGHMGI-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 239000007858 starting material Substances 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
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 in the gas phase
- C01C1/0405—Preparation of ammonia by synthesis in the gas phase 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 .
Claims (1)
- EMI0002.0089 PATENTANSPRUCIi Verfahren zur Herstellung des 2-Diphenvl- m:ethyl-piperidlins der Formel EMI0002.0093 dadurch -ekennzeiehnet, dass man das 2-Di- phenyl-methyl-pyrid'in mit Hydrierenden Mit teln behandelt. UNTERANSPRUCH EMI0002.0098 Verfahren <SEP> nach <SEP> Patentanspi-iich, <SEP> dadurch gekennzeichnet, dass man mit Wasserstoff in Gegenwart eines Ed"elmetallkatalysators hy driert.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH320133T | 1953-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH320133A true CH320133A (de) | 1957-03-15 |
Family
ID=4497885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH320133D CH320133A (de) | 1953-07-06 | 1953-07-06 | Verfahren zur Herstellung einer neuen Piperidinverbindung |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT190058B (de) |
| BE (1) | BE530124A (de) |
| CH (1) | CH320133A (de) |
| DE (1) | DE1095280B (de) |
| FR (1) | FR1167463A (de) |
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 (fr) * | 1950-12-05 | 1953-04-24 | Schering Corp | Procede de preparation de piperidines substituees. |
-
1953
- 1953-07-06 CH CH320133D patent/CH320133A/de unknown
-
1954
- 1954-06-21 AT AT190058D patent/AT190058B/de active
- 1954-07-01 DE DEC9591A patent/DE1095280B/de active Pending
- 1954-07-05 FR FR1167463D patent/FR1167463A/fr not_active Expired
- 1954-07-05 BE BE530124A patent/BE530124A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT190058B (de) | 1957-06-11 |
| BE530124A (fr) | 1957-08-30 |
| FR1167463A (fr) | 1958-11-25 |
| DE1095280B (de) | 1960-12-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH320133A (de) | Verfahren zur Herstellung einer neuen Piperidinverbindung | |
| AT237591B (de) | Verfahren zur Herstellung des neuen 1-Cyclohexyl-2-aminopropanons-(1) und dessen Salze | |
| DE2123319A1 (de) | S-Sulfonamido^-hydroxyphenyl^piperidylcarbinole, Verfahren zu ihrer Herstellung und Arzeneipräparate | |
| AT221502B (de) | Verfahren zur Herstellung neuer basischer Phenoläther und ihrer Salze | |
| DE895903C (de) | Verfahren zur Herstellung neuer basisch substituierter Halogenaryl-pyridyl-alkanone | |
| DE2065019C3 (de) | Neue antiphlogistisch wirksame Aralkylverbl ndungen | |
| AT228211B (de) | Verfahren zur Herstellung von neuen Phenothiazinderivaten, sowie von Säureadditionssalzen und quartären Salzen dieser Phenothiazinderivate | |
| AT204033B (de) | Verfahren zur Herstellung des neuen 3-(p-Amino-benzolsulfonamido)-2-phenyl-pyrazols | |
| AT214427B (de) | Verfahren zur Herstellung neuer basischer Phenoläther | |
| AT237596B (de) | Verfahren zur Herstellung des neuen 1-Cyclohexyl-2-aminopropanos-(1) und dessen Salze | |
| AT201247B (de) | Verfahren zur Herstellung des neuen 6-Hydroxy-3:5-cyclopregnan-20-ons | |
| AT257610B (de) | Verfahren zur Herstellung von neuen Estern substituierter 8-Hydroxychinoline | |
| AT262287B (de) | Verfahren zur Herstellung von dem neuen 2-Isopropyl-1,3-di-(4-piperidyl)-propan und den Salzen dieser Verbindung | |
| AT235292B (de) | Verfahren zur Herstellung des neuen 1-(2-Pyridyl)-1-phenyl-2-(3-chlorphenyl)-propan-2-ols | |
| DE565799C (de) | Verfahren zur Herstellung von 1-Pheny1-3-methy1-4-alkyl- und -4-aralkylpyrazolonen | |
| DE423026C (de) | Verfahren zur Darstellung eines Bz-Tetrahydrooxychinolins | |
| AT200136B (de) | Verfahren zur Herstellung von neuen tertiären Aminen der Tetrahydrofuranreihe | |
| AT233552B (de) | Verfahren zur Herstellung von neuen Dibenzocycloheptadien-Derivaten und ihren Salzen | |
| AT258947B (de) | Verfahren zur Herstellung von neuen substituierten Hydrazinverbindungen und ihren Salzen | |
| AT201248B (de) | Verfahren zur Herstellung des neuen 6-Hydroxy-3:5-cyclopregnan-20-ons | |
| AT210891B (de) | Verfahren zur Herstellung von neuen Methylpiperidylpentanol-estern | |
| DE952896C (de) | Verfahren zur Herstellung von Diaminonaphthophenazinen | |
| DE925166C (de) | Verfahren zur Herstellung von AEpfelsaeure-dialdehyd | |
| AT257579B (de) | Verfahren zur Herstellung neuer substituierter Benzamide und deren Säureadditionssalze | |
| AT339277B (de) | Verfahren zur herstellung von neuen 11-amino-benzo(b) bicyclo (3,3,1)nona-3,6a(10a)dienen und deren saureadditionssalzen |