CH358080A - Verfahren zur Herstellung von bisher unbekannten, in m-Stellung eines Phenylrestes substituierten Diphenylamin-Derivaten - Google Patents
Verfahren zur Herstellung von bisher unbekannten, in m-Stellung eines Phenylrestes substituierten Diphenylamin-DerivatenInfo
- Publication number
- CH358080A CH358080A CH358080DA CH358080A CH 358080 A CH358080 A CH 358080A CH 358080D A CH358080D A CH 358080DA CH 358080 A CH358080 A CH 358080A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- previously unknown
- phenyl radical
- derivatives substituted
- Prior art date
Links
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- MRYWSLAXVVHDBL-UHFFFAOYSA-N 3-iodo-n-phenylaniline Chemical compound IC1=CC=CC(NC=2C=CC=CC=2)=C1 MRYWSLAXVVHDBL-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NDJOOOBYISLBRN-UHFFFAOYSA-N N-phenyl-3-phenylsulfanylaniline Chemical compound C1(=CC=CC=C1)SC=1C=C(C=CC=1)NC1=CC=CC=C1 NDJOOOBYISLBRN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000010438 heat treatment Methods 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YDHVAPBSJDSJRG-UHFFFAOYSA-N 2-(3-iodoanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(I)=C1 YDHVAPBSJDSJRG-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- FFCSRWGYGMRBGD-UHFFFAOYSA-N 3-iodoaniline Chemical compound NC1=CC=CC(I)=C1 FFCSRWGYGMRBGD-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
- C07D211/26—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 nitrogen 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung von bisher unbekannten, in m-Stellung eines Phenylrestes substituierten Diphenylamin-Derivaten Es wurde gefunden, dass man zu bisher unbekann- ten, in m-Stellung eines Phenylrestes substituierten Diphenylaminen der Formel I EMI1.1 Ri = Aryl oder Aralkyt, R2 = niederes Alkyl, gelangen kann, indem man ein sekundäres Amin der Formel II EMI1.2 mit einem Piperidin der Formel III EMI1.3 <tb> Halogen-CH2-CH2 <SEP> lll <tb> <SEP> 1 <tb> <SEP> Rz <tb> worin Halogen für Chlor, Brom oder Jod steht, kondensiert. Beispiel N- [m-Phenylrnercapto-plzenyl]-N- [2- (N'-methyl- piperidyl-2')-dthyl-1]-arzilin Man kondensiert m-Jod-anilin (Sdp. 145-146 C/ 15 mm) mit dem Kaliumsalz der o-Chlor-benzoesäure und decarboxyliert die entstandene N- (m-Jod phenyl)-anthranilsäure (Smp. 168-170 C) durch Erhitzen und anschliessende Destillation zum N- (m- Jod-phenyl)-anilin (Sdp. 140-143 C/0, 05 mm Hg). Das erhaltene N- (m-Jod-phenyl)-anilin wird durch Kondensation mit Natrium-thiophenolat in Anwesenheit von Kupferpulver zum N- (m-Phenylmercapto- phenyl)-anilin (Sdp. 176 CiO, 005 mm Hg) umgesetzt. 30,0 g N- (m-Phenylmercapto-phenyl)-anilin werden in 150 cm3 abs. Xylol gelöst, mit 5,10 g feinpulverisiertem Natriumamid versetzt und während 2 Stunden bei einer Badtemperatur von 180 C zum Sieden am Rückfluss erhitzt. Darauf lässt man, ohne das Erhitzen zu unterbrechen, innerhalb von 11/2 Stunden 19,7 g 2-(N-Methyl-piperidyl-2')-1-chlor-äthan (Sdp. 84 C/10 mm Hg), gelöst in 20 cm3 abs. Xylol, zutropfen und erhitzt, ohne das Rühren zu unterbrechen, das Gemisch während weiteren 3 Stund'en. Alsdann wird abgekühlt und das überschüssige Natriumamid durch Zusatz von 10 g Ammoniumchlorid zersetzt. Die dreimal mit je 100 cm3 Wasser gewaschene Xylollösung wird mit 250 cm3 15 /oiger wässriger Weinsäure ausgezogen. Man schüttelt den Weinsäureauszug mit 100 cm3 Benzol und macht ihn mit 75 cm3 konz. Natronlauge phenolphthalein-alkalisch. Die Lösung der ausgeschiedenen öligen Base in 200 cm3 Benzol wird mit 100 cm3 Wasser ausgeschüttelt, über Pottasche getrocknet, filtriert und unter vermindertem Druck eingedampft. Der Rückstand wird im Hochvakuum destilliert, wobei die unter 0,01 mm Hg bei 217-219 C übergehende Hauptfraktion aufgefangen wird. Das analysenreine N- [m-Phenyl-mercapto-phe- nylu-N- [2-(N'-methyl-piperidyl-2')-äthyl-1]-anilin hat den Sdp. 218 C bei 0,01 mm Hg. Beim Versetzen einer auf 0 C abgekühlten Lösung von 24,3 g der freien Base in 150 cm3 abs. Al- kohol mit äthanolischem Chlorwasserstoff fällt das Chlorhydrat aus, welches aus 175 cm3 abs. Alkohol kochend umkristallisiert wird. Das analysenreine Chlorhydrat des N-[m-Phenylmercapto-phenyl]-N-[2- -methyl-piperidyl-2')-äthyl-1]-anilins hat den konstanten Smp. 176-178 C, sint. ab 172 C.
Claims (1)
- PATENTANSPRUCH Verfahren zur Herstellung von bisher unbekannten Diphenylamin-Derivaten der Formel I EMI2.1 <SEP> I <SEP> I <tb> <SEP> N <tb> <SEP> CH2/\ <tb> <SEP> CH2 <SEP> kN/ <tb> <SEP> N <tb> <SEP> N <tb> Ri <SEP> = <SEP> Aryl <SEP> oder <SEP> Aralkyl, <tb> R <SEP> = <SEP> niederes <SEP> Alkyl, <SEP> R2 <tb> dadurch gekennzeichnet, dass man ein sekundäres Amin der Formel II EMI2.2 mit einem Piperidin der Formel III EMI2.3 <SEP> (H) <tb> Halogen-CHz-CHz <SEP> III <tb> <SEP> N <tb> <SEP> t <tb> <SEP> R2 <tb> svorin Halogen für Chlor, Brom oder Jod steht, kondensiert.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH358080T | 1957-08-05 | ||
| CH355145T | 1957-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH358080A true CH358080A (de) | 1961-11-15 |
Family
ID=25737146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH358080D CH358080A (de) | 1957-08-05 | 1957-08-05 | Verfahren zur Herstellung von bisher unbekannten, in m-Stellung eines Phenylrestes substituierten Diphenylamin-Derivaten |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH358080A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9862679B2 (en) | 2013-03-08 | 2018-01-09 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Office Of Technology Transfer, National Institutes Of Health | Potent and selective inhibitors of monoamine transporters; method of making; and use thereof |
| US11365195B2 (en) | 2017-11-13 | 2022-06-21 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Atypical inhibitors of monoamine transporters; method of making; and use thereof |
-
1957
- 1957-08-05 CH CH358080D patent/CH358080A/de unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9862679B2 (en) | 2013-03-08 | 2018-01-09 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Office Of Technology Transfer, National Institutes Of Health | Potent and selective inhibitors of monoamine transporters; method of making; and use thereof |
| US10590074B2 (en) | 2013-03-08 | 2020-03-17 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Potent and selective inhibitors of monoamine transporters; method of making; and use thereof |
| US10913711B2 (en) | 2013-03-08 | 2021-02-09 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Potent and selective inhibitors of monoamine transporters; method of making; and use thereof |
| US11555013B2 (en) | 2013-03-08 | 2023-01-17 | The Usa, As Represented By The Secretary, Dhhs | Potent and selective inhibitors of monoamine transporters; method of making; and use thereof |
| US11365195B2 (en) | 2017-11-13 | 2022-06-21 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Atypical inhibitors of monoamine transporters; method of making; and use thereof |
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