CH469657A - Process for the preparation of new 2-amino-benzylamines - Google Patents
Process for the preparation of new 2-amino-benzylaminesInfo
- Publication number
- CH469657A CH469657A CH39669A CH3966966A CH469657A CH 469657 A CH469657 A CH 469657A CH 39669 A CH39669 A CH 39669A CH 3966966 A CH3966966 A CH 3966966A CH 469657 A CH469657 A CH 469657A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- methylenedioxybenzyl
- formula
- alkyl radical
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- GVOYKJPMUUJXBS-UHFFFAOYSA-N 2-(aminomethyl)aniline Chemical class NCC1=CC=CC=C1N GVOYKJPMUUJXBS-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- -1 methylenedioxy group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- FBDGHIJTDKJJJV-UHFFFAOYSA-N 6-(ethylaminomethyl)-1,3-benzodioxol-5-amine Chemical compound NC1=C(CNCC)C=C2C(=C1)OCO2 FBDGHIJTDKJJJV-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 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
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OMKYSUZBOAZYSW-UHFFFAOYSA-N 2,3,4-trimethoxy-6-[(propan-2-ylamino)methyl]aniline Chemical compound NC1=C(CNC(C)C)C=C(C(=C1OC)OC)OC OMKYSUZBOAZYSW-UHFFFAOYSA-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
- WHMUTLQBGGCCJU-UHFFFAOYSA-N 6-[(dimethylamino)methyl]-1,3-benzodioxol-5-amine Chemical compound NC1=C(CN(C)C)C=C2C(=C1)OCO2 WHMUTLQBGGCCJU-UHFFFAOYSA-N 0.000 description 1
- KAPAJCPOBXIQRP-UHFFFAOYSA-N 6-amino-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C(N)=CC2=C1OCO2 KAPAJCPOBXIQRP-UHFFFAOYSA-N 0.000 description 1
- HFGDQMJDPOALEW-UHFFFAOYSA-N CCNCC(C=C(C(OC)=C1OC)OC)=C1N Chemical compound CCNCC(C=C(C(OC)=C1OC)OC)=C1N HFGDQMJDPOALEW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- MSNJUJBWTJTCSV-UHFFFAOYSA-N NC1=C(CN(CC)CC)C=C2C(=C1)OCO2 Chemical compound NC1=C(CN(CC)CC)C=C2C(=C1)OCO2 MSNJUJBWTJTCSV-UHFFFAOYSA-N 0.000 description 1
- BFRWHLRQKJTAAG-UHFFFAOYSA-N NC1=C(CN2CCOCC2)C(=C(C(=C1)OC)OC)OC Chemical compound NC1=C(CN2CCOCC2)C(=C(C(=C1)OC)OC)OC BFRWHLRQKJTAAG-UHFFFAOYSA-N 0.000 description 1
- QSUUAPLPYVNBSO-UHFFFAOYSA-N NC1=C(CNC(C)C)C=C2C(=C1)OCO2 Chemical compound NC1=C(CNC(C)C)C=C2C(=C1)OCO2 QSUUAPLPYVNBSO-UHFFFAOYSA-N 0.000 description 1
- HYTZVGLWXKTIHO-UHFFFAOYSA-N NC1=C(CNC)C=C2C(=C1)OCO2 Chemical compound NC1=C(CNC)C=C2C(=C1)OCO2 HYTZVGLWXKTIHO-UHFFFAOYSA-N 0.000 description 1
- HRKJPFKMKTYYFZ-UHFFFAOYSA-N NC1=C(CNCCCC)C=C2C(=C1)OCO2 Chemical compound NC1=C(CNCCCC)C=C2C(=C1)OCO2 HRKJPFKMKTYYFZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical class NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 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
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von neuen 2-Amino-benzylaminen Die Erfindung betrifft ein Verfahren zur Herstellung von neuen 2-Amino-benzylaminen der Formel
EMI0001.0001
sowie von deren physiologisch verträglichen Additions salzen mit anorganischen oder organischen Säuren.
In der obigen Formel bedeuten einen niederen Alkylrest, der gegebenenfalls R durch eine niedere Alkoxygruppe substituiert ist, oder einen Cycloalkylrest, R2 ein Wasserstoffatom oder einen niederen Alkyl rest, oder zusammen mit R1 mit und dem Stickstoffatom einen gesättigten 5- oder 6gliedrigen heterocyclischen Ring, der durch ein weiteres Heteroatom unterbrochen und/oder durch einen niederen Alkylrest substituiert sein kann, zwei der Reste R3 bis R6 niedere Alkoxygruppen, ins besondere Methoxygruppen, oder, sofern sie benach bart sind, zusammen eine Methylendioxygruppe und die restlichen zwei der Reste R3 bis R6 Wasserstoffatome oder niedere Alkoxygruppen, insbesondere Methoxy- gruppen.
Erfindungsgemäss erfolgt die Herstellung der neuen Verbindungen nach für die Synthese substituierter Amino-benzylamine üblichem Verfahren, indem man einen 2-Aminobenzaldehyd der Formel
EMI0001.0007
mit einem Amin der Formel
EMI0001.0008
reduktiv kondensiert.
Die Umsetzung wird vorzugsweise mittels kataly tisch erregtem Wasserstoff in Gegenwart eines Edel- metallkatalysators wie Platin oder Palladium oder in Gegenwart von Raney-Nickel bei Raumtemperaturen oder mässig erhöhten Temperaturen in Anwesenheit eines inerten Lösungsmittels, beispielsweise Methanol, Äthanol oder Dioxan, durchgeführt.
Die erfindungsgemäss erhältlichen freien Basen las sen sich durch Umsetzung mit anorganischen oder or ganischen Säuren in ihre physiologisch verträglichen Säureadditionssalze überführen. Als Säuren können bei spielsweise Chlorwasserstoffsäure, Bromwasserstoffsäu re, Schwefelsäure, Phosphorsäure, Oxalsäure, Bern steinsäure, Weinsäure, Zitronensäure, Maleinsäure oder Fumarsäure verwendet werden.
Die als Ausgangsstoffe verwendeten 2-Aminobenzal- dehyde der Formel II sind literaturbekannt.
Die neuen Verbindungen und ihre Salze weisen wertvolle pharmakologische Eigenschaften auf, insbe sondere wirken sie sekretolytisch und hustenstillend. Das nachstehende Beispiel dient zur näheren Erläu terung der Erfindung: Beispiel N-(2-Amino-4,5-methylendioxybenzyl)-äthylamin: 5 g 2-Amino-4,5-methylendioxy-benzaldehyd wur den in Methanol mit überschüssiger methanolischer Äthylaminlösung versetzt. Nach Stehen über Nacht wur de die Lösung mit Raney-Nickel als Katalysator hy driert. Nachdem die berechnete Menge Wasserstoff auf genommen war, wurde vom Katalysator abfiltriert, das Filtrat eingedampft und der Rückstand in Äther auf genommen.
Nach Waschen mit Wasser wurde über Aluminiumoxyd filtriert. Das Filtrat wurde eingedampft und der Rückstand im Vakuum destilliert. Ausbeute an N-(2-Amino-4,5-methylendioxybenzyl)-äthylamin: 1 g; Kp0.1 110 bis 115 C, F. 58 C. In gleicher Weise wurden erhalten: N-(2-Amino-4,5-methylendioxybenzyl)-methylamin vom KP1,5 mm Hg 136-138 C; N-(2-Amino-4,5-methylendioxybenzyl)-äthylamin vom F. 58 C; N-(2-Amino-4,5-methylendioxybenzyl)-n-propylamin vom Kp0,22 mm Hg 136-138 C; N-(2-Amino-4,5-methylendioxybenzyl)-isopropylamin vom Kp0,6 mm a, 133 C; N-(2-Amino-4,5-methylendioxybenzyl)-n-butylamin Vom Kp0,04 mm Hg 132 C; N-(2-Amino-4,5-methylendioxybenzyl)-sek.butylamin vom Kp0,06 mm Hg 123 C; N-(2-Amino-4,5-methylendioxybenzyl)-isobutylamin vom F.<B>53'</B> C;
N-(2-Amino-4,5-methylendioxybenzyl)-tert. butylamin vom F. 70 C; N-(2-Amino-4,5-methylendioxybenzyl)-2-methoxyäthyl- amin vom Kp0,2 mm Hg 140 C; N-(2-Amino-4,5-methylendioxybenzyl)-dimethylamin vom Kp0,2 mm H, 1031 C; N-(2 Amino-4,5-methylendioxybenzyl)-diäthylamin vom Kp0 2 mm Hg 135 C; N-(2 Amino-4,5-methylendioxybenzyl)-äthylcyclohexyl- amin vom F. 80 C; N-(2-Amino-4,5-methylendioxybenzyl)-pyrrolidin vom F. 50 C; N-(2-Amino-4,5-methylendioxybenzyl)-morpholin vom F. 80 C; N-(2-Amino-4,5-methylendioxybenzyl)-piperidin vom F. 74 C; N-(2-Amino-4,5-methylendioxybenzyl)-N'-methyl- piperazin vom F. 87 C;
N-(2-Amino-4,5-dimethoxybenzyl)-äthylamin vom F.
des Dihydrochlorids 90 C; N-(2-Amino-4,5-dimethoxybenzyl)-n-propylamin vom F. des Dihydrochlorids 187 C; N-(2-Amino-4,5-dimethoxybenzyl)-n butylamin vom KP0,05 mm H, 150 C; N-(2-Amino-4,5-dimethoxybenzyl)-sek.butylamin vom F.<B>610</B> C; N-(2-Amino-4,5-dimethoxybenzyl)-isobutylamin vom KP0,05 mm H, 131 C; N-(2-Amino-4,5-dimethoxybenzyl)-tert.butylamin vom F. 98 C; N-(2-Amino-4,5-methoxybenzyl)-äthylcyclohexylamin vom F. des Dihydrochlorids 180 C; N-(2-Amino-4,5-dimethoxybenzyl)-piperidin vom F. des Dihydrochlorids l97 C; N-(2-Amino-3,5-dimethoxybenzyl)-thylamin vom F. des Oxalats 180 C; N-(2-Amino-3,5-dimethoxybenzyl)-äthylamin vom F. des des Oxalats 180 C; N-(2-Amino-4,5,6-trimethoxybenzyl)-äthylamin vom F. des Oxalats 173' C; N-(2-Amino-4,5,6-trimethoxybenzyl)-piperidin vom F.
des Dihydrochlorids 174 C; N-(2-Amino-4,5,6-trimethoxybenzyl)-morpholin vom F.
des Dihydrochlorids 183 C; N-(2-Amino-3,4,5-trimethoxybenzyl)-äthylamin vom KP0,8 mm $, 140 C; N-(2-Amino-3,4,5-trimethoxybenzyl)-isopropylamin vom F. des Dihydrochlorids 192 C.
Process for the preparation of new 2-amino-benzylamines The invention relates to a process for the preparation of new 2-amino-benzylamines of the formula
EMI0001.0001
as well as their physiologically acceptable addition salts with inorganic or organic acids.
In the above formula, a lower alkyl radical, which R is optionally substituted by a lower alkoxy group, or a cycloalkyl radical, R2 is a hydrogen atom or a lower alkyl radical, or together with R1 with and the nitrogen atom is a saturated 5- or 6-membered heterocyclic ring which interrupted by a further hetero atom and / or substituted by a lower alkyl radical, two of the radicals R3 to R6 lower alkoxy groups, in particular methoxy groups, or, if they are adjacent, together a methylenedioxy group and the remaining two of the radicals R3 to R6 hydrogen atoms or lower alkoxy groups, especially methoxy groups.
According to the invention, the new compounds are prepared by the processes customary for the synthesis of substituted aminobenzylamines, by adding a 2-aminobenzaldehyde of the formula
EMI0001.0007
with an amine of the formula
EMI0001.0008
reductively condensed.
The reaction is preferably carried out by means of catalytically excited hydrogen in the presence of a noble metal catalyst such as platinum or palladium or in the presence of Raney nickel at room temperatures or at moderately elevated temperatures in the presence of an inert solvent, for example methanol, ethanol or dioxane.
The free bases obtainable according to the invention can be converted into their physiologically compatible acid addition salts by reaction with inorganic or organic acids. The acids used can be, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, oxalic acid, succinic acid, tartaric acid, citric acid, maleic acid or fumaric acid.
The 2-aminobenzaldehydes of the formula II used as starting materials are known from the literature.
The new compounds and their salts have valuable pharmacological properties, in particular they have a secretolytic and cough suppressant effect. The following example serves to explain the invention in greater detail: Example N- (2-Amino-4,5-methylenedioxybenzyl) -ethylamine: 5 g of 2-amino-4,5-methylenedioxy-benzaldehyde were added to methanol with excess methanolic ethylamine solution . After standing overnight, the solution was hydrated with Raney nickel as a catalyst. After the calculated amount of hydrogen had been taken up, the catalyst was filtered off, the filtrate was evaporated and the residue was taken up in ether.
After washing with water, it was filtered through aluminum oxide. The filtrate was evaporated and the residue was distilled in vacuo. Yield of N- (2-amino-4,5-methylenedioxybenzyl) ethylamine: 1 g; Bp 0.1 110 to 115 C, m.p. 58 C. The following were obtained in the same way: N- (2-amino-4,5-methylenedioxybenzyl) methylamine with a KP 1.5 mm Hg 136-138 C; N- (2-Amino-4,5-methylenedioxybenzyl) ethylamine with a melting point of 58 ° C; N- (2-Amino-4,5-methylenedioxybenzyl) -n-propylamine, bp 0.22 mm Hg 136-138 C; N- (2-Amino-4,5-methylenedioxybenzyl) isopropylamine, bp 0.6 mm a, 133 C; N- (2-Amino-4,5-methylenedioxybenzyl) -n-butylamine. Bp 0.04 mm Hg, 132 C; N- (2-Amino-4,5-methylenedioxybenzyl) -sec.butylamine with a boiling point of 0.06 mm Hg 123 C; N- (2-Amino-4,5-methylenedioxybenzyl) isobutylamine of F. 53 'C;
N- (2-Amino-4,5-methylenedioxybenzyl) tert. butylamine with a melting point of 70 ° C; N- (2-Amino-4,5-methylenedioxybenzyl) -2-methoxyethylamine with a boiling point of 0.2 mm Hg 140 C; N- (2-Amino-4,5-methylenedioxybenzyl) dimethylamine, b.p. 0.2 mm H, 1031 C; N- (2-amino-4,5-methylenedioxybenzyl) diethylamine of Kp0 2 mm Hg 135 C; N- (2-amino-4,5-methylenedioxybenzyl) -äthylcyclohexyl- amine with a melting point of 80 ° C .; N- (2-Amino-4,5-methylenedioxybenzyl) pyrrolidine of mp 50 ° C; N- (2-Amino-4,5-methylenedioxybenzyl) morpholine with a melting point of 80 ° C; N- (2-Amino-4,5-methylenedioxybenzyl) piperidine, mp 74 ° C; N- (2-amino-4,5-methylenedioxybenzyl) -N'-methyl-piperazine of m.p. 87 C;
N- (2-Amino-4,5-dimethoxybenzyl) ethylamine from F.
of the dihydrochloride 90 C; N- (2-Amino-4,5-dimethoxybenzyl) -n-propylamine from the temperature of the dihydrochloride 187 C; N- (2-amino-4,5-dimethoxybenzyl) -n butylamine of KP 0.05 mm H, 150 ° C; N- (2-amino-4,5-dimethoxybenzyl) -sec.butylamine from F. 610 C; N- (2-Amino-4,5-dimethoxybenzyl) isobutylamine of KP 0.05 mm H, 131 C; N- (2-amino-4,5-dimethoxybenzyl) -tert.butylamine with a melting point of 98 ° C; N- (2-Amino-4,5-methoxybenzyl) ethylcyclohexylamine from the temperature of the dihydrochloride 180 ° C .; N- (2-Amino-4,5-dimethoxybenzyl) piperidine from the temperature of the dihydrochloride 197 C; N- (2-Amino-3,5-dimethoxybenzyl) -thylamine from the temperature of the oxalate 180 C; N- (2-Amino-3,5-dimethoxybenzyl) ethylamine from the temperature of the oxalate 180 C; N- (2-Amino-4,5,6-trimethoxybenzyl) ethylamine from the F. of the oxalate 173 'C; N- (2-Amino-4,5,6-trimethoxybenzyl) piperidine from F.
of the dihydrochloride 174 C; N- (2-Amino-4,5,6-trimethoxybenzyl) -morpholine from F.
of the dihydrochloride 183 C; N- (2-amino-3,4,5-trimethoxybenzyl) ethylamine of KP0.8 mm $, 140 ° C; N- (2-Amino-3,4,5-trimethoxybenzyl) isopropylamine from the F. of the dihydrochloride 192 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET0028357 | 1965-04-09 | ||
| CH385266A CH469656A (en) | 1965-04-09 | 1966-03-17 | Process for the preparation of new 2-amino-benzylamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH469657A true CH469657A (en) | 1969-03-15 |
Family
ID=25694007
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH39669A CH469657A (en) | 1965-04-09 | 1966-03-17 | Process for the preparation of new 2-amino-benzylamines |
| CH39769A CH469658A (en) | 1965-04-09 | 1966-03-17 | Process for the preparation of new 2-amino-benzylamines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH39769A CH469658A (en) | 1965-04-09 | 1966-03-17 | Process for the preparation of new 2-amino-benzylamines |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH469657A (en) |
-
1966
- 1966-03-17 CH CH39669A patent/CH469657A/en unknown
- 1966-03-17 CH CH39769A patent/CH469658A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH469658A (en) | 1969-03-15 |
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