DE731561C - Process for the preparation of hydrogenated isoquinoline compounds which are aralkyl-substituted in the nitrogen-containing nucleus and which contain free hydroxyl groups in an aromatic nucleus - Google Patents
Process for the preparation of hydrogenated isoquinoline compounds which are aralkyl-substituted in the nitrogen-containing nucleus and which contain free hydroxyl groups in an aromatic nucleusInfo
- Publication number
- DE731561C DE731561C DEK155512D DEK0155512D DE731561C DE 731561 C DE731561 C DE 731561C DE K155512 D DEK155512 D DE K155512D DE K0155512 D DEK0155512 D DE K0155512D DE 731561 C DE731561 C DE 731561C
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- nucleus
- nitrogen
- hydroxyl groups
- aralkyl
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung von im gtickstoffhaltigen Kern aralkylsubstituierten und in einem aromatischen Kern freie Hydroxylgruppen enthaltenden hydrierten Isochinolinverbindungen Das Hauptpatent 728 326 zu dem Zusatzpatent 73o 667 des vorliegenden Patents hat ein Verfahren zur Herstellung von im stickstoffhaltigen Kern aralkylsubstituierten und in einem aromatischen Kern freie Hydroxylgruppen enthaltenden hydrierten Isochinolinverbindungen, zum Gegenstand, das dadurch gekennzeichnet ist, daß man im stickstoffhaltigen Kern aralkylsubstituierte, nur in einem aromatischen Kern mindestens zwei freie, vorzugsweise in o-Stellung zueinander befindliche Hy droxylgruppen enthaltende, gegebenenfalls noch weiter, z. B. durch Kohlenwasserstoffreste, substituierte, nicht oder nur teilweise hydrierte Isochinolinverbindungen oder deren quartäre Ammoniumsalze in an sich bekannter Weise hydriert. -Das Zusatzpatent 73o 667 hat ein weiteres Verfahren zur Herstellung von im stickstofflialtigen Kern aralkylsubstituierten und in nur einem aromatischen Kern mindestens zwei freie, vorzugsweise in o-Stellung zueinander befindliche Hydroxylgruppen enthaltenden, gegebenenfalls noch weiter, z. B. durch Kohlenwasserstoffreste, substituierten hydrierten Isochinolinverbindungen zum Gegenstand, das dadurch gekennzeichnet ist, daß man von im stickstoffhaltigen Kern aralkylensubstituierten, nicht -oder nur teilweise hydrierten Isochinolinverbindungen oder deren quartären Ammoniumsalzen ausgeht und diese derart hydriert, daß sowolil die Doppelbindungen des Pyridinringes als auch die aliphatischen Doppelbindungen des Aralkylenrestes in einfache Bindungen übergeführt werden.Aralkyl-substituted method for the preparation of gtickstoffhaltigen core and in an aromatic nucleus free hydroxyl group-containing hydrogenated isoquinoline The main patent 728 326 has the addition Patent 73o 667 of the present patent is a process for the preparation of nitrogen-containing core aralkyl-substituted, and containing in an aromatic nucleus free hydroxyl groups hydrogenated isoquinoline , to the subject, which is characterized in that in the nitrogen-containing nucleus aralkyl-substituted, only in an aromatic nucleus containing at least two free, preferably in the o-position to each other Hy hydroxyl groups, optionally further, z. B. hydrogenated by hydrocarbon radicals, substituted, not or only partially hydrogenated isoquinoline compounds or their quaternary ammonium salts in a manner known per se. The additional patent 73o 667 has a further process for the preparation of aralkyl-substituted in the nitrogen-containing nucleus and containing at least two free hydroxyl groups in only one aromatic nucleus, preferably in the o-position to one another, optionally even further, e.g. B. by hydrocarbon radicals, substituted hydrogenated isoquinoline compounds to the subject, which is characterized in that aralkylenesubstituted in the nitrogen-containing nucleus, non-or only partially hydrogenated isoquinoline compounds or their quaternary ammonium salts and these are hydrogenated in such a way that both the double bonds of the pyridine ring and the aliphatic double bonds of the aralkylene radical are converted into single bonds.
Es wurde nun gefunden, daß man solche hydrierten Isochinolinverbindungen auch dadurch herstellen kann, daß man im stickstoffhaltigen Kern aralkylensubstituierte, nur in einem Benzolkern mindestens zwei freie, vorzugsweise in o-Stellung zueinander befindliche Hydroxylgruppen enthaltende, gegebenenfalls noch weiter, z. B. durch gesättigte oder ungesättigte Kohlenwasserstoffreste, substituierte Tetraliv(Iroisocliinolinverbinclungen in an sich bekannter Weise derart livclriert, daß die Aralkylensubstituenten in Äralkvlsubstittienten übergeführt werden.It has now been found that such hydrogenated isoquinoline compounds can be obtained can also be prepared by aralkylene-substituted in the nitrogen-containing nucleus, only in one benzene nucleus at least two free, preferably in O-position to one another containing hydroxyl groups, optionally also further, e.g. B. substituted by saturated or unsaturated hydrocarbon radicals Tetralive (Iroisocliinolinverbinclungen in a manner known per se colored in such a way, that the aralkylene substituents are converted into aralkylene substituents.
Die Hydrierung wird z. B. katalytisch in Gegenwart von Hydrierungsl@atalysatoren, wie Platinmohr, Platinoxyd, Palladium oder Palladiumtierkohle, oder zweckmäßig durch andere Reduktionsmittel, z. B. Jodwasserstoffsäure, vorgenommen, die eine Kohlenstoffdoppelbindung zu einer einfachen Bindung livdrieren.The hydrogenation is z. B. catalytically in the presence of Hydrogenierungsl @ atalysatoren, such as platinum black, platinum oxide, palladium or palladium animal charcoal, or expediently through other reducing agents, e.g. B. hydriodic acid made, which has a carbon double bond livdrive to a simple tie.
Die Ausgangsstoffe für das Verfahren können dadurch hergestellt werden, daß man entsprechend substituierteTetrallydroisochiiloline mit entsprechend substituierten Aralkylenhalogeniden umsetzt oder daß inan entsprechend substituierte ß-(3, 4-Dioxvl)Iienyl)-äthylamitte mit ungesättigten Aralkvleilaldehvden zu Tetrahydroisochmolinen kondensiert.The starting materials for the process can be prepared by reacting correspondingly substituted tetrallydroisochiilolines with correspondingly substituted aralkylene halides or by condensing correspondingly substituted β- (3, 4-dioxvl) iienyl) -ethylamittees with unsaturated aralkvleilaldehydes to give tetrahydroisochmolines.
Von bekannten Verbindungen kommen den erfindungsgemäß hergestellten Verbindungen Tetraliydropapaverolin und Laudanosolin nahe, die jedoch im Gegensatz zu den erfindungsgemäßen erliältlicllen Verbindungen in jedem Benzolkern je -zwei freie Hydroxylgruppen enthalten.Known compounds include those prepared according to the invention Compounds tetraliydropapaverolin and laudanosolin close, however, in contrast to the compounds according to the invention obtainable in each benzene nucleus two each contain free hydroxyl groups.
Diese beiden bekannten Verbindungen wirken weder einetisch noch analgetisch. Weiterhin sindLatidanosolin-3', 4.'-dimethvläther und Laudanosolin-a'-monoinetliylätlier bekannt, Verbindungen also, die zwar in einen Benzolkern zwei freie Hy droxyIgruppen, darüber hinaus aber ein anderen Benzolkern zwei verätherte bzw. eine verätlierte und eine freie Hydroxylgruppe enthalten. Diese beiden Verbindungen wirken stark toxisch und zeigen keine ausgeprägte analgetische Wirkung. Im Gegensatz zti den vier bekannten Verbindtin-en zeichnen sich die erfindtingsgeniiiß erhältlichen Verbindungen durch ihre guten analgetischen und einetischen Wirkungen bc@i nur geringer Toxizität aus.These two well-known compounds are neither toxic nor analgesic. Furthermore, latidanosolin-3 ', 4'-dimethyl ether and laudanosolin-a'-monoinetliyl ether known, compounds that, although two free hydroxyl groups in a benzene nucleus, in addition, however, another benzene nucleus, two etherified and one tethered and contain a free hydroxyl group. These two connections are powerful toxic and show no pronounced analgesic effect. In contrast zti the The compounds obtainable according to the invention are characterized by four known compounds due to their good analgesic and chemical effects bc @ i only low toxicity the end.
Beispiele i. Herstellung von i, 3-Diiiiethyl-2-(^,-plielvlprol>yl)-ti, 7-cüoxv-r, a, 3, .I-tetralivdroisochinolin.Examples i. Preparation of i, 3-Diiiiethyl-2 - (^, - plielvlprol> yl) -ti, 7-cüoxv-r, a, 3, .I-tetralivdroisoquinoline.
g Bromhydrat des 1, 3-Dimet@vl-2-(^@-1#henylallvl)-6, 7-dioxy-i, 2,
3, .I-tetrahydroisocliinolins vorn F. Leg bis 151`' (mit i Kristallalkohol) werden
mit 5o ccin konstant siedender- Jodwasserstoffsä ure unter Zusatz von etwas Phosphor
25 Minuten 7u111 lebhaften Sieden erhitzt. Die Reduktion ist dann beendet.
Man dampft im Vakuum zur Trockne, zielet den Rückstand finit viel heihein Wasser
aus, filtriert, entfärbt die Lösung finit etwas schwefliger Säure, fällt die Base
mit Soda und äthert aus. Aus der über Natriumsulfat gut getrockneten Ätherlösung
wird mit ätherischer Salzsäure das Chlorlivdrat der in der i@berschrift genannten
Verbindung erhalten, das aus Methanol mit 1 Mol. Kristallmethanol auskristallisiert,
welches im @'aku@mexs@kkator bei Zimnierteinperatur noch nicht abgegeben wird. Das
Chlorhydrat hat folgende Konstitution
Es schmilzt bei 121 bis i23'' unter Aufschäumen und stimmt in jeder Hinsicht mit
denn aus Methanol umkristallisierten Chlorlivdrat der im Patent 711 o98 beschriebenen
Verbindung gleicher Konstitution überein.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEK155512D DE731561C (en) | 1939-09-03 | 1939-09-03 | Process for the preparation of hydrogenated isoquinoline compounds which are aralkyl-substituted in the nitrogen-containing nucleus and which contain free hydroxyl groups in an aromatic nucleus |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEK155512D DE731561C (en) | 1939-09-03 | 1939-09-03 | Process for the preparation of hydrogenated isoquinoline compounds which are aralkyl-substituted in the nitrogen-containing nucleus and which contain free hydroxyl groups in an aromatic nucleus |
Publications (1)
Publication Number | Publication Date |
---|---|
DE731561C true DE731561C (en) | 1943-02-15 |
Family
ID=7253287
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEK155512D Expired DE731561C (en) | 1939-09-03 | 1939-09-03 | Process for the preparation of hydrogenated isoquinoline compounds which are aralkyl-substituted in the nitrogen-containing nucleus and which contain free hydroxyl groups in an aromatic nucleus |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE731561C (en) |
-
1939
- 1939-09-03 DE DEK155512D patent/DE731561C/en not_active Expired
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