CH456586A - Process for the production of new amines - Google Patents
Process for the production of new aminesInfo
- Publication number
- CH456586A CH456586A CH1676567A CH1676567A CH456586A CH 456586 A CH456586 A CH 456586A CH 1676567 A CH1676567 A CH 1676567A CH 1676567 A CH1676567 A CH 1676567A CH 456586 A CH456586 A CH 456586A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- acid
- dependent
- salts
- starting material
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 150000001412 amines Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- -1 alkali borohydrides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229960004365 benzoic acid Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- RHCSKNNOAZULRK-UHFFFAOYSA-N mescaline Chemical compound COC1=CC(CCN)=CC(OC)=C1OC RHCSKNNOAZULRK-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BZCOSCNPHJNQBP-UPHRSURJSA-N (z)-2,3-dihydroxybut-2-enedioic acid Chemical compound OC(=O)C(\O)=C(\O)C(O)=O BZCOSCNPHJNQBP-UPHRSURJSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Chemical class 0.000 description 1
- 229910000564 Raney nickel Chemical class 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical class [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission 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
- 230000001914 calming effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000001558 histaminolytic effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical class [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 229940107700 pyruvic acid Drugs 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
- 230000000384 rearing effect Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung neuer Amine
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Verbindungen der Formel
EMI1.1
worin A die Dimethylamino-oder Diäthylaminogruppe darstellt oder ihrer Salze.
Die neuen Verbindungen besitzen wertvolle pharmakologische Eigenschaften. So zeigen sie eine zentralhemmende Wirkung, die durch einen Antagonismus gegenüber psychomotorischen Stoffen, wie z. B. Mescalin, sowie durch eine Hemmung der spinalen Reflexübertragung gekennzeichnet ist, sowie eine histaminolytische Wirkung und können daher als psychotrope, beruhigende Medikamente in der Human- und Veterinärmedizin Verwendung finden. Sie eignen sich aber auch als Zusätze zu Tierfutter, da sie eine bessere Nahrungsverwertung bewirken. Weiter können die neuen Verbindungen als Ausgangs- oder Zwischenprodukte für die Her stellung anderer wertvoller Verbindungen dienen.
Das erfindungsgemässe Verfahren zur Herstellung der neuen Verbindungen ist dadurch gekennzeichnet, dass man in einer Verbindung der Formel
EMI1.2
worin X einen der oben definierten Gruppe der Formel -CHA entsprechender Rest ist, der eine sich vom Stickstoffatom an ein benachbartes Kohlenstoffatom erstreckende Doppelbindung aufweist, die CN-Doppel- bindung reduziert.
Die Reduktion der Azomethinbindung kann in üblicher Weise erfolgen, z. B. unter Anwendung der üblichen Reduktionsmittel, vornehmlich Metallhydriden, z. B. Di-leichtmetallhydriden, wie Alkaliborhydriden, oder von katalytisch aktiviertem Wasserstoff, wobei als Katalysatoren vor allem Platinoxid oder Raney-Nickel zu erwähnen sind, oder auch Ameisensäure.
Die Ausgangsstoffe können auch in Form eines unter den Reaktionsbedingungen gebildeten Reaktionsgemisches eingesetzt werden.
So kann man beispielsweise von Verbindungen der Formel II ausgehen, worin X die Formylgruppe bedeutet, und sie unter geeigneten reduzierenden Bedingungen mit Dimethylamin oder Diäthylamin umsetzen. Dabei erhält man als Zwischenprodukt eine Verbindung der Formel II, worin X eine Dimethyl- oder Diäthylammoniummethylgruppe bedeutet, die dann ohne Isolierung erfindungsgemäss reduziert wird.
Ferner kann man z. B. von einer Verbindung der Formel II ausgehen, worin X die Methylaminomethylgruppe oder Aminomethylgruppe darstellt und diese unter reduzierenden Bedingungen mit Formaldehyd umsetzen, wobei intermediär ein Ausgangsstoff der Formel II entsteht, der dann ohne Isolierung erfindungsgemäss reduziert werden kann.
Die Ausgangsstoffe sind bekannt oder können nach an sich bekannten Verfahren gewonnen werden.
Die neuen Verbindungen können je nach den Re aktionsbedingungen und Ausgangsstoffen in freier Form oder in Form ihrer Salze erhalten werden. Die Salze der neuen Verbindungen können in an sich bekannter Weise in die freien Verbindungen übergeführt werden, z. B. Säureadditionssalze, durch Reaktion mit einem basischen Mittel. Anderseits können gegebenenfalls erhaltene freie Basen mit anorganischen oder organischen Säuren Salze bilden. Zur Herstellung von Säureadditions salzen werden insbesondere therapeutisch verwendbare Säuren verwendet, z. B.
Halogenwasserstoffsäuren, bei spieisweise Salzäure oder Bromwasserstoffsäure, Perchlorsäure, Salpetersäure oder Thiocyansäure, Schwefeloder Phosphorsäuren, oder organische Säuren, wie Ameisensäure, Essigsäure, Propionsäure, Glykolsäure, Mitch- säure, Brenztraubensäure, Oxalsäure, Malonsäure, Bernsteinsäure, Maleinsäure, Fumarsäure, Äpfelsäure, Weinsäure, Zitronensäure, Ascorbinsäure, Hydroxy:
maleinsäure, Dihydroxymaleinsäure, Benzoesäure, Phenylessigsäure, 4Amino-benzoesäure, 4-Hydroxybenzoesäure, Anthranilsäure, Zimtsäure, Mandelsäure, Salicylsäure, 4Amino-salicylsäure, 2-Phenoxybenzoesäure, 2-Acetoxy-benzoesäure, Methansulfonsäure, Äthansulfonsäure, Hydroxyäthansulfonsäure, BenzolsuIfonsäure, p-Toluol-sulfonsäure, Naphthalinsulfon- säure oder Sulfanilsäure, oder Methionin, Tryptophan, Lysin oder Arginin. Dabei können Mono-oder Polysalze vorliegen.
Die neuen Verbindungen können als Heilmittel in Form von pharmazeutischen Präparaten verwendet werden, welche diese Verbindungen zusammen mit pharmazeutischen, organischen oder anorganischen, festen oder flüssigen Trägerstoffen, die für enterale, z. B. orale, oder parenterale Gabe geeignet sind, enthalten.
Die neuen Verbindungen können auch in der Tiermedizin, z. B. in einer der oben genannten Formen, oder bei der Aufzucht und Ernährung von Tieren in Form von Futtermitteln oder von Zusatzmitteln. für Tierfutter verwendet werden.
In den folgenden Beispielen sind die Temperaturen in Ceisiusgraden angegeben.
Beispiel 1
Eine Lösung von 23 g 2-Chlor-9-methylamino methyl- 9,10 -dihydro - 9,10- ,L)-anhracen in 100 ml Ameisensäure und 10 ml 3.9 % igem Formalin wird während 4 Stunden auf 900 erwärmt. Anschliessend gibt man 500 ml Wasser zu und stellt durch Zugabs von iOn Natronlauge alkalisch. Es scheidet sich ein Öl aus, das mit Äther extrahiert wird. Nach dem Trocknen und Eindampfen des Lösungsmittels verbleibt das 2-Chlor-9-dimethylaminomethyl-9, 1 O-dihydro 9,10athano(1 ,2)-anthracen der Formel
EMI2.1
dessen Hydrochlorid bei 244-2450 schmilzt (Ausbeute 93 /0).
Beispiel 2
Durch Umsetzen von 2-Chlor-9, 10-dihydro-9, 10- äthanol-(1,2)-9-anthracenaldehyd mit Diäthylamin in Äthanol und Reduktion des so erhaltenen Kondensa tionsproduktes mit Wasserstoff in Gegenwart von Raney-Nickei kann man das 2-Chlor-9-diäthylamino-methyl-9, 1 O-dihydro- 9, 10-äthano-(1, 2)-anthracen der Formel
EMI2.2
erhalten, dessen Hydrochlorid bei 2310 schmilzt.
Process for the production of new amines
The invention relates to a process for the preparation of compounds of the formula
EMI1.1
wherein A represents the dimethylamino or diethylamino group or their salts.
The new compounds have valuable pharmacological properties. So they show a central inhibiting effect, which by an antagonism to psychomotor substances, such as. B. mescaline, and is characterized by an inhibition of the spinal reflex transmission, and a histaminolytic effect and can therefore be used as psychotropic, calming drugs in human and veterinary medicine. But they are also suitable as additives to animal feed, as they bring about better food utilization. The new compounds can also serve as starting materials or intermediates for the manufacture of other valuable compounds.
The inventive method for preparing the new compounds is characterized in that in a compound of the formula
EMI1.2
wherein X is a radical corresponding to the group of the formula -CHA defined above, which has a double bond extending from the nitrogen atom to an adjacent carbon atom, which reduces the CN double bond.
The azomethine bond can be reduced in a conventional manner, e.g. B. using the usual reducing agents, mainly metal hydrides, z. B. Di-light metal hydrides, such as alkali borohydrides, or of catalytically activated hydrogen, platinum oxide or Raney nickel as catalysts, or formic acid.
The starting materials can also be used in the form of a reaction mixture formed under the reaction conditions.
For example, one can start from compounds of the formula II in which X is the formyl group, and react them with dimethylamine or diethylamine under suitable reducing conditions. A compound of the formula II in which X is a dimethyl or diethylammonium methyl group, which is then reduced according to the invention without isolation, is obtained as an intermediate product.
Furthermore, you can z. B. start from a compound of formula II in which X represents the methylaminomethyl group or aminomethyl group and react this under reducing conditions with formaldehyde, whereby a starting material of formula II is formed as an intermediate, which can then be reduced according to the invention without isolation.
The starting materials are known or can be obtained by processes known per se.
The new compounds can be obtained in free form or in the form of their salts, depending on the reaction conditions and starting materials. The salts of the new compounds can be converted into the free compounds in a manner known per se, eg. B. acid addition salts, by reaction with a basic agent. On the other hand, any free bases obtained can form salts with inorganic or organic acids. For the preparation of acid addition salts are used in particular therapeutically useful acids, for. B.
Hydrogen halides, sometimes hydrochloric acid or hydrobromic acid, perchloric acid, nitric acid or thiocyanic acid, sulfuric or phosphoric acids, or organic acids such as formic acid, acetic acid, propionic acid, glycolic acid, mitic acid, pyruvic acid, oxalic acid, malonic acid, succinic acid, maleic acid, Citric Acid, Ascorbic Acid, Hydroxy:
maleic acid, dihydroxymaleic acid, benzoic acid, phenylacetic acid, 4-amino-benzoic acid, 4-hydroxybenzoic acid, anthranilic acid, cinnamic acid, mandelic acid, salicylic acid, 4-amino-salicylic acid, 2-phenoxybenzoic acid, 2-acetoxy-benzoic acid, 2-acetoxy-benzoic acid, benzenesulphonic acid, ethanesulphonic acid, toluene-benzoic acid, benzenesulphonic acid, toluenesulphonic acid sulfonic acid, naphthalenesulfonic acid or sulfanilic acid, or methionine, tryptophan, lysine or arginine. Mono- or poly-salts can be present here.
The new compounds can be used as medicaments in the form of pharmaceutical preparations, which these compounds together with pharmaceutical, organic or inorganic, solid or liquid carriers which are suitable for enteral, e.g. B. oral or parenteral administration are suitable.
The new compounds can also be used in veterinary medicine, e.g. B. in one of the above forms, or in the rearing and nutrition of animals in the form of feed or additives. be used for animal feed.
In the following examples the temperatures are given in Ceisius degrees.
example 1
A solution of 23 g of 2-chloro-9-methylamino methyl-9,10-dihydro-9,10-, L) -anhracene in 100 ml of formic acid and 10 ml of 3.9% formalin is heated to 900 for 4 hours. Then 500 ml of water are added and the mixture is made alkaline by adding iOn sodium hydroxide solution. An oil separates which is extracted with ether. After drying and evaporation of the solvent, the 2-chloro-9-dimethylaminomethyl-9, 1 O-dihydro 9,10athano (1, 2) -anthracene of the formula remains
EMI2.1
its hydrochloride melts at 244-2450 (yield 93/0).
Example 2
By reacting 2-chloro-9, 10-dihydro-9, 10-ethanol (1,2) -9-anthracenaldehyde with diethylamine in ethanol and reducing the condensation product thus obtained with hydrogen in the presence of Raney-Nickei you can 2-chloro-9-diethylamino-methyl-9, 1 O-dihydro-9, 10-ethano- (1, 2) -anthracene of the formula
EMI2.2
obtained, the hydrochloride of which melts at 2310.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1676567A CH456586A (en) | 1960-11-29 | 1965-12-10 | Process for the production of new amines |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH483965A CH398569A (en) | 1960-11-29 | 1960-11-29 | Process for the preparation of new 9-aminoalkyl-9,10-dihydro-9,10-ethano- (1,2) -anthracenes |
| CH1676567A CH456586A (en) | 1960-11-29 | 1965-12-10 | Process for the production of new amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH456586A true CH456586A (en) | 1968-07-31 |
Family
ID=25696382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1676567A CH456586A (en) | 1960-11-29 | 1965-12-10 | Process for the production of new amines |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH456586A (en) |
-
1965
- 1965-12-10 CH CH1676567A patent/CH456586A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2500110A1 (en) | 3-ARYLOXY-3-PHENYLPROPYLAMINE AND THE PROCESS FOR THEIR MANUFACTURING | |
| DD262226A5 (en) | PROCESS FOR THE PREPARATION OF PHENYL ALKYLOMINE DERIVATIVES | |
| DE2163911B2 (en) | 2-aminomethyl-phenols, process for the preparation thereof and medicaments containing them | |
| DE2115926B2 (en) | 1- (4-HYDROXY-3-DIMETHYLAMINOSULFAMIDOPHENYL) -2-AMINOETHANE DERIVATIVES, THE PROCESS FOR THEIR PREPARATION AND AGENTS CONTAINING THESE | |
| DE2633889C2 (en) | Novel aminobenzocycloheptene derivatives and their salts, processes for their preparation and pharmaceutical compositions | |
| DE2458638C2 (en) | 4'-substituted 2-methyl-3-piperidinopropiophenone derivatives, processes for their production and pharmacological preparations which contain them | |
| DE2351281B2 (en) | Aminophenylethanolamine derivatives, their production and use | |
| CH456586A (en) | Process for the production of new amines | |
| DE2144077C3 (en) | New Hydroxyäthylaminoalkylpiperazines and processes for their preparation | |
| CH438352A (en) | Process for the preparation of diphenylalkylamines | |
| DE1931927A1 (en) | New cyclohexylamine derivatives | |
| EP0031456B1 (en) | Substituted 4-amino-2,6-diaryl-tetrahydrothiopyranes, their acid-addition salts, processes for their preparation and pharmaceutical compositions | |
| AT230366B (en) | Process for the preparation of new 9-aminoalkyl-9,10-dihydro-9,10-ethano- (1 ', 2') -anthracenes and their salts or quaternary ammonium compounds | |
| DE2530768C3 (en) | PhenoxyaUcylaminpyridyläther, process for their production and pharmaceutical preparations containing them | |
| DE1670378A1 (en) | Process for the preparation of a compound from phenylbutazone and ss-diaethylaminoaethylamide of p-chlorophenoxyacetic acid | |
| AT357165B (en) | METHOD FOR PRODUCING NEW CHINA ZOLINE DERIVATIVES AND THEIR SALTS | |
| AT237597B (en) | Process for the production of new propylamine derivatives and their salts | |
| AT258930B (en) | Process for the preparation of new phenothiazine derivatives and their salts | |
| CH481868A (en) | Process for the production of new amines | |
| AT288393B (en) | Process for the preparation of new cinnamic acid amides | |
| AT238180B (en) | Process for the preparation of new pyrrolidine compounds | |
| CH524568A (en) | N-(Lower alkyl)-phenylisopropylamines | |
| DE1620223A1 (en) | Process for the preparation of oxaphenanthridines | |
| DE2423897A1 (en) | NEW N- (P-FLUOROBENZOYLPROPYL) -4- PIPERIDYLAMIDES AND THE METHOD FOR THEIR PRODUCTION | |
| CH536271A (en) | CNS active ethano:anthracene derivs. - prepd. by reacting corresp. parent anthracene with e.g. alkyl halide in presence of a base |