DE1147945B - Process for the preparation of 1-amino-2- [6'-methoxyindolyl- (3 ')] propane - Google Patents
Process for the preparation of 1-amino-2- [6'-methoxyindolyl- (3 ')] propaneInfo
- Publication number
- DE1147945B DE1147945B DEL32121A DEL0032121A DE1147945B DE 1147945 B DE1147945 B DE 1147945B DE L32121 A DEL32121 A DE L32121A DE L0032121 A DEL0032121 A DE L0032121A DE 1147945 B DE1147945 B DE 1147945B
- Authority
- DE
- Germany
- Prior art keywords
- methoxyindolyl
- propane
- amino
- nitro
- preparation
- 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.)
- Pending
Links
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title claims description 19
- 239000001294 propane Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- -1 methylmagnesium halide Chemical class 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 5
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 5
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- 229940075930 picrate Drugs 0.000 claims description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims description 4
- JTEFJNIWWXTBMP-UHFFFAOYSA-N 6-methoxy-1h-indole-3-carbaldehyde Chemical compound COC1=CC=C2C(C=O)=CNC2=C1 JTEFJNIWWXTBMP-UHFFFAOYSA-N 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Description
Verfahren zur Herstellung von 1-Amino-2-[6'-methoxyindolyl-(3@]-propan Gegenstand der Patentanmeldung L 30993 IVd/12p ist ein Verfahren zur Herstellung von 1-Amino-2-[6'-methoxyindolyl-(31]-propan der Formel das dadurch gekennzeichnet ist, daß man ein 6-Methoxyindolylmagnesiumhalogenid in an sich bekannter Weise mit a-Brompropionitril in Gegenwart eines organischen Lösungsmittels umsetzt, das erhaltene 2-[6'-Methoxyindolyl-(37]-propionitril mit einem organischen Lösungsmittel extrahiert. und in ammoniakalisch alkoholischer Lösung in Gegenwart eines Nickelkatalysators hydriert, das entstandene 1-Amino-2-[6'-methoxyindolyl-(31]-propan mit Pikrinsäure umsetzt, das Pikrat mit einem Alkalihydroxyd zersetzt und die freie Base mit einem organischen Lösungsmittel extrahiert.Process for the preparation of 1-amino-2- [6'-methoxyindolyl- (3 @] - propane The subject of patent application L 30993 IVd / 12p is a process for the preparation of 1-amino-2- [6'-methoxyindolyl- (31 ] propane of the formula which is characterized in that a 6-methoxyindolylmagnesium halide is reacted in a manner known per se with a-bromopropionitrile in the presence of an organic solvent, the 2- [6'-methoxyindolyl- (37] propionitrile obtained is extracted with an organic solvent and in ammoniacal alcoholic solution hydrogenated in the presence of a nickel catalyst, the resulting 1-amino-2- [6'-methoxyindolyl- (31] -propane is reacted with picric acid, the picrate is decomposed with an alkali hydroxide and the free base is extracted with an organic solvent.
Es wurde nun gefunden, daß man gleichfalls zu dem 1-Amino-2-[6'-methoxyindolyl-(37]-propan gelangt, wenn man 6-Methoxy-3-formylindol der Formel I in an sich bekannter Weise mit Nitromethan in Gegenwart eines organischen Lösungsmittels, z. B. Benzol, und einer organischen Base, z. B. Piperidin, umsetzt, das erhaltene 1-Nitro-2-[6'-methoxyindolyl-(31]-äthen der Formel II mit einem Methylmagnesiumhalogenid kondensiert, das entstandene 1-Nitro-2-[6'-methoxyindolyl-(3@]-propan der Formel III mit einem Mischmetallhydrid, vorzugsweise mit Lithiumaluminiumhydrid in Tetrahydrofuran, reduziert, das 1-Amino-2-[6'-methoxyindolyl-(37]-propan der Formel IV mit Pikrinsäure umsetzt und das Pikrat mit einem Alkalihydroxyd, vorzugsweise Lithiumhydroxyd, zersetzt.It has now been found that 1-amino-2- [6'-methoxyindolyl- (37] propane obtained when 6-methoxy-3-formylindole of the formula I is used in a manner known per se with nitromethane in the presence of an organic solvent, e.g. B. Benzene, and an organic base, e.g. B. piperidine, converts the 1-nitro-2- [6'-methoxyindolyl- (31] -ethene obtained) of formula II condensed with a methyl magnesium halide, the resulting 1-nitro-2- [6'-methoxyindolyl- (3 @] - propane of the formula III with a mixed metal hydride, preferably with lithium aluminum hydride in tetrahydrofuran, the 1-amino-2- [6'-methoxyindolyl- (37] propane of Formula IV reacts with picric acid and the picrate with an alkali hydroxide, preferably Lithium hydroxide, decomposed.
Das folgende Reaktionsschema veranschaulicht das erfindungsgemäße Verfahren: Das folgende Beispiel erläutert das Verfahren. Beispiel In einen mit Rückflußkühler mit Wasserabscheider ausgestatteten Kolben gibt man 120 g - 6-Methoxy-3-formylindol (hergestellt nach der im Journal of the Chemical Society, 1938, S.97 bis 101, beschriebenen Arbeitsweise), 5400 ccm Benzol, 38,4 ccm Piperidin und 83,5 g Nitromethan. Das Reaktionsgemisch wird 6 Stunden zum Sieden unter Rückfluß erhitzt, und während dieser Zeit werden 12 ccm Wasser aufgefangen. Nach dem Abkühlen läßt man über Nacht stehen. Der gebildete Niederschlag wird abgesaugt und durch zweimaliges Anreiben mit Benzol gewaschen. Nach dem Trocknen erhält man 128 g des rohen Reaktionsproduktes (F. 202°C), das man durch Umkristallisieren aus Äthanol reinigt. Die Ausbeute beträgt 63,5 g (42,5%). Das 1-Nitro-2-[6'-methoxyindolyl-(3@]-äthen liegt in Form ziegelroter prismatischer Kristalle vor, die in Aceton und Tetrahydrofuran und in Alkohol in der Wärme löslich und in Äther, Benzol und Chloroform unlöslich sind.The following reaction scheme illustrates the process according to the invention: The following example explains the procedure. EXAMPLE 120 g of 6-methoxy-3-formylindole (prepared according to the procedure described in the Journal of the Chemical Society, 1938, pp. 97 to 101), 5400 ccm of benzene, 38, are placed in a flask equipped with a reflux condenser with a water separator. 4 cc piperidine and 83.5 g nitromethane. The reaction mixture is refluxed for 6 hours, during which time 12 cc of water are collected. After cooling, it is left to stand overnight. The precipitate formed is filtered off with suction and washed by rubbing twice with benzene. After drying, 128 g of the crude reaction product (mp 202 ° C.) are obtained, which are purified by recrystallization from ethanol. The yield is 63.5 g (42.5%). The 1-nitro-2- [6'-methoxyindolyl- (3 @] - ethene is in the form of brick-red prismatic crystals, which are soluble in acetone and tetrahydrofuran and in alcohol in the heat and insoluble in ether, benzene and chloroform.
Zur Herstellung des 1-Nitro-2-[6'-methoxyindölyl-(3')]-propans gibt man eine Lösung von 50 g des 1-Nitro-2-[6'-methoxyindolyl-(3')]-äthens in 11 Tetrahydrofuran in eine ätherische Lösung von Methylmagnesiumjodid, die aus 150 g Methyljodid und 22,3 g Magnesium erhalten worden ist, unter Einleiten von Stickstoff und bei äußerer Kühlung mit einem Eisbad. Die Zugabe -der Nitroverbindung erfolgt in der Weise, daß die Temperatur zwischen 15 und 20°C bleibt und dauert etwa 11/2 Stunden. Das Reaktionsgemisch wird dann 4 Stunden gerührt und danach mit 1250 ccm einer gesättigten Ammoniumchloridlösung versetzt. Man setzt das Rühren noch 15 Minuten fort, trennt die wäßrige Phase ab und extrahiert sie mit Äther. Die vereinigten organischen Lösungen werden mit einer 5%igen Natriumbisulfitlösung und dann mit Wasser gewaschen, über Natriumsulfat getrocknet und abfiltriert. Das Filtrat wird im Vakuum zur Trockne eingedampft. Der aus 50 g (93%) des rohen. Reaktionsproduktes bestehende Rückstand wird ohne Reinigung für die nächste Verfahrensstufe verwendet.For the preparation of the 1-nitro-2- [6'-methoxyindölyl- (3 ')] - propane are a solution of 50 g of 1-nitro-2- [6'-methoxyindolyl- (3 ')] -ethens in 11 tetrahydrofuran in an essential solution of methyl magnesium iodide, which is made up of 150 g of methyl iodide and 22.3 g of magnesium has been obtained, with the introduction of nitrogen and with external Cooling with an ice bath. The addition of the nitro compound takes place in the manner that the temperature remains between 15 and 20 ° C and lasts about 11/2 hours. That The reaction mixture is then stirred for 4 hours and then with 1250 ccm of a saturated one Ammonium chloride solution added. Stirring is continued for a further 15 minutes and separated the aqueous phase and extracted with ether. The combined organic solutions are washed with a 5% sodium bisulfite solution and then with water, over Dried sodium sulfate and filtered off. The filtrate becomes dry in vacuo evaporated. The one made from 50 g (93%) of the crude. Reaction product existing residue is used for the next stage of the process without purification.
Man gibt eine Lösung von 50 g des 1-Nitro-2-[6'-methoxyindolyl-(3@]-propans in 1000 ccm Tetrahydrofuran innerhalb von 11/2 Stunden zu einer Lithiumaluminiumhydridlösung aus 25 g Lithiumaluminiumhydrid in 750 ccm Tetrahydrofuran, wobei man ständig ein gelindes Rückflußsieden aufrechterhält. Man setzt das Erhitzen noch 4 Stunden fort, zersetzt nach dem Abkühlen den Hydridüberschuß durch Zugabe von Wasser, filtriert, wäscht das ausgefallene Aluminiumhydroxyd mit Tetrahydrofuran und dampft die vereinigten Lösungen im Vakuum zur Trockne. Nach dem Aufnehmen des Rückstandes in Methylenchlorid extrahiert man mit 5%iger wäßriger Essigsäure, bringt den pH-Wert der Extrakte mit 5 n-Natronlauge auf 10 und extrahiert mit Methylenchlorid. Die Extrakte werden nach dem Trocknen und Abfiltrieren im Vakuum zur Trockne eingedampft. Man erhält 25 g des rohen 1-Amino-2-[6'-methoxyindolyl-,(3@-propans, das man durch Auflösen in 100 ccm Äthanol und Zugabe einer 5%igen alkoholischen Pikrinsäurelösung in das Pikrat überführt. Nach der Fällung des Tryptaminsalzes kühlt man 1 Stunde auf Eis, filtriert, saugt ab, wäscht durch Anreiben mit Äthanol und trocknet. Man erhält 44,5 g (48%) des Pikrates (F. 242'C), das rot gefärbt ist und dessen Mikroanalyse und IR-Spektrum seine Identität mit dem nach dem Verfahren der Patentanmeldung L 30993 IVd/12 p erhaltenen Produkte bestätigt. Das Amin wird dann mit Lithiumhydroxyd in Freiheit gesetzt, und man erhält das 1-Amino-2-[6'-methoxyindolyl-(3')]-propan, das auf Grund seines IR-Spektrums mit dem nach dem Verfahren der Patentanmeldung L 30993 IVd/12 p erhaltenen Endprodukt identisch ist.A solution of 50 g of 1-nitro-2- [6'-methoxyindolyl- (3 @] propane) is added in 1000 cc of tetrahydrofuran within 11/2 hours to a lithium aluminum hydride solution from 25 g of lithium aluminum hydride in 750 cc of tetrahydrofuran, with one constantly maintains a gentle reflux. The heating is continued for another 4 hours, after cooling, decomposes the excess hydride by adding water, filtered, washes the precipitated aluminum hydroxide with tetrahydrofuran and evaporates the combined Solutions in a vacuum to dryness. After taking up the residue in methylene chloride extraction with 5% aqueous acetic acid brings the pH of the extracts with it 5 N sodium hydroxide solution to 10 and extracted with methylene chloride. The extracts are after evaporated to dryness in vacuo before drying and filtering off. 25 g are obtained of the crude 1-amino-2- [6'-methoxyindolyl-, (3 @ -propane, which can be obtained by dissolving in 100 cc of ethanol and adding a 5% alcoholic picric acid solution to the picrate convicted. After the tryptamine salt has precipitated, it is cooled on ice for 1 hour, filtered, sucks off, washes by rubbing with ethanol and dries. 44.5 g (48%) are obtained of picrates (F. 242'C), which is colored red, and its microanalysis and IR spectrum his identity with the according to the procedure of the patent application L 30993 IVd / 12 p products received. The amine is then released with lithium hydroxide set, and 1-amino-2- [6'-methoxyindolyl- (3 ')] propane is obtained, which is due to its IR spectrum with that according to the method of patent application L 30993 IVd / 12 p final product obtained is identical.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1147945X | 1958-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1147945B true DE1147945B (en) | 1963-05-02 |
Family
ID=9646167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEL32121A Pending DE1147945B (en) | 1958-01-08 | 1959-01-02 | Process for the preparation of 1-amino-2- [6'-methoxyindolyl- (3 ')] propane |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1147945B (en) |
-
1959
- 1959-01-02 DE DEL32121A patent/DE1147945B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
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