CH280677A - Process for the production of a heterocyclic nitrogen compound. - Google Patents
Process for the production of a heterocyclic nitrogen compound.Info
- Publication number
- CH280677A CH280677A CH280677DA CH280677A CH 280677 A CH280677 A CH 280677A CH 280677D A CH280677D A CH 280677DA CH 280677 A CH280677 A CH 280677A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- nitrogen compound
- heterocyclic nitrogen
- pyrrolidine
- benzyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 229910017464 nitrogen compound Inorganic materials 0.000 title description 4
- -1 heterocyclic nitrogen compound Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung einer heterocyclischen Stickstoffverbindung. Es wurde gefunden, dass heterocyclische Stickstoffverbindungen des Aufbaues
EMI0001.0005
worin X und Y aromatische oder aralipha- tisehe Reste mit einem Kern, Z den Rest einer gesättigten heterocyclischen Stickstoffverbin dung, die mit Stickstoff an das Kohlenstoff atom einer CH-Gruppe gebunden ist, und n mindestens 2 bedeutet, sehr wertvolle Pro dukte sind.
In Form ihrer Salze, insbesondere der Hydrochloride, oder der von ihnen abge leiteten quaternären Ammoniumverbindungen zeigen diese Verbindungen bemerkenswerte antiliisiaminische Wirksamkeit, zum Teil sind sie darin solchen entsprechend aufgebauten, be kannten Verbindungen überlegen, die an Stelle des heterocyelisehen Ringes Z eine durch zwei offenkettige aliphatische Reste substituierte Aminogruppe enthalten.
Dies ist besonders überraschend, da nach den Angaben der Lite ratur in antihistaminisch wirkenden ou-Di- alkylamino-ätliern der Ersatz der Dialli#-1- aminogruppe durch einen heterocyelischen Rest die physiologische Wirksamkeit herab setzt.
Besondere Wirksamkeit zeigen solche Ver bindungen der oben angegebenen Formel, in denen die Reste X oder Y Phenyl-, Tolyl-, Benzyl- oder Phenyläthylreste sind, die Zahl n = 2 oder 3 ist und der heterocyclische Rest von Pyrrolidin oder seinen Homologen, z. B. C-Methyl-pyrrolidin, Piperidin oder Hexa- methylenimin, abgeleitet ist.
Gegenstand des Patentes ist ein Verfahren zur Herstellung von N-(ss-N'-Benzyl-N'-phe- nyl-ainino-äthyl)-pyrrolidin, welches dadurch gekennzeichnet ist, dass man N-(fl-Chlor- äthyl)-pyrrolidin mit N-Benz yl-anilin konden- siert.
Das Produkt ist kristallin und farblos. Es schmilzt bei 194 bis 195 und siedet unter 2 nim Druck bei 197 bis 199 . <I>Beispiel:</I> 31 Teile N-(ss-Chlor-ät.hyl)-pyrrolidin-hy- droehlorid werden mit<B>110</B> Teilen N-Benzyl-ani- lin zusammen in 400 Teilen Alkohol gelöst und unter Zusatz von 0,5 Teilen Kupferpulver 15 Stunden zum Sieden unter Rückflzisskühlung erhitzt. Nach dem Abfiltrieren und Abtreiben des Alkohols versetzt man mit verdünnter Na tronlauge bis zur alkalischen Reaktion und destilliert das abgeschiedene<B>01</B> im Vakuum.
plan erhält zunächst das überschüssige N-Ben- zyl-anilin und dann als bei 197 bis 199 unter 2 mni Druck siedende Fraktion das N-(ss-N'- Phenyl-N'-benzyl-amino-äthyl)-pyrrolidin. Das Produkt ist kristallin und farblos; es schmilzt bei 194 bis<B>1</B>95<B>0</B>.
Process for the production of a heterocyclic nitrogen compound. It has been found that heterocyclic nitrogen compounds of the structure
EMI0001.0005
where X and Y are aromatic or araliphatic radicals with a nucleus, Z is the radical of a saturated heterocyclic nitrogen compound bonded with nitrogen to the carbon atom of a CH group, and n is at least 2, are very valuable products.
In the form of their salts, in particular the hydrochloride, or the quaternary ammonium compounds derived from them, these compounds show remarkable anti-lysiaminic activity, in part they are superior to those correspondingly structured, known compounds that, instead of the heterocyclic ring Z, have one open-chain aliphatic Contain radicals substituted amino group.
This is particularly surprising since, according to the literature, in antihistaminic ou-dialkylamino-ethers, the replacement of the diali # -1-amino group by a heterocyclic residue reduces the physiological effectiveness.
Particular effectiveness is shown by those compounds of the formula given above in which the radicals X or Y are phenyl, tolyl, benzyl or phenylethyl radicals, the number n = 2 or 3 and the heterocyclic radical of pyrrolidine or its homologues, eg. B. C-methyl-pyrrolidine, piperidine or hexamethylene imine is derived.
The subject of the patent is a process for the production of N- (ss-N'-benzyl-N'-phenyl-ainino-ethyl) -pyrrolidine, which is characterized in that N- (fl-chloro-ethyl) - pyrrolidine condensed with N-benzyl aniline.
The product is crystalline and colorless. It melts at 194 to 195 and boils at 197 to 199 under 2 nm pressure. <I> Example: </I> 31 parts of N- (ss-chloro-ethyl) -pyrrolidine-hydrochloride are combined with <B> 110 </B> parts of N-benzyl-aniline in 400 parts Dissolved alcohol and refluxed for 15 hours with the addition of 0.5 part of copper powder. After the alcohol has been filtered off and stripped off, dilute sodium hydroxide solution is added until an alkaline reaction occurs, and the deposited 01 is distilled in vacuo.
plan first receives the excess N-benzyl-aniline and then as a fraction boiling at 197 to 199 under 2 mni pressure, the N- (ss-N'-phenyl-N'-benzyl-amino-ethyl) -pyrrolidine. The product is crystalline and colorless; it melts at 194 to <B> 1 </B> 95 <B> 0 </B>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE280677X | 1948-12-10 | ||
| DE285687X | 1948-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH280677A true CH280677A (en) | 1952-01-31 |
Family
ID=33098874
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH280677D CH280677A (en) | 1948-12-10 | 1949-11-25 | Process for the production of a heterocyclic nitrogen compound. |
| CH285687D CH285687A (en) | 1948-12-10 | 1949-11-25 | Process for the production of a heterocyclic nitrogen compound. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH285687D CH285687A (en) | 1948-12-10 | 1949-11-25 | Process for the production of a heterocyclic nitrogen compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH280677A (en) |
-
1949
- 1949-11-25 CH CH280677D patent/CH280677A/en unknown
- 1949-11-25 CH CH285687D patent/CH285687A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH285687A (en) | 1952-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2807623C2 (en) | 2-Phenoxyphenyl-pyrrolidine derivatives, their salts, processes for their production and pharmaceutical preparations containing them | |
| DE3420193A1 (en) | NEW SUBSTITUTED PYRROLIDINONES, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS | |
| DE1445904A1 (en) | Process for the preparation of 4-imidazolidone compounds | |
| DE2362754C2 (en) | Oxazoline compounds containing cyclopropylalkylamino radicals, processes for their preparation and medicaments containing these compounds | |
| CH280677A (en) | Process for the production of a heterocyclic nitrogen compound. | |
| DE2522218C3 (en) | Composition for human or veterinary medicine, methylamine derivatives and processes for their preparation | |
| DE1695104A1 (en) | Active sulfonamides | |
| CH392497A (en) | Process for the production of new benzenesulfonyl-cyclohexyl-ureas | |
| DE2310827C3 (en) | Phenylalanine derivatives heterocyclically substituted in the phenyl nucleus | |
| AT208872B (en) | Process for the preparation of new 1,4-diazacycloheptanes | |
| DE2613328C3 (en) | l-methyl-2- (m-trifluoromethyl-phenyl) -ethylamide of p-pentylaminophenoxyacetic acid, a process for its production and pharmaceuticals | |
| AT345852B (en) | PROCESS FOR MANUFACTURING NEW FURYL URINES | |
| DE1470010B1 (en) | N- (beta-guanidinoaethyl) -6-azaspiro [2.5] octane and process for its preparation | |
| DE842345C (en) | Process for the preparation of heterocyclic nitrogen compounds | |
| AT237603B (en) | Process for the production of new o-toluidides | |
| AT226239B (en) | Process for the production of new benzylguanidines | |
| DE3000624A1 (en) | 3,4-EPOXY-PYRROLIDINE AND PHARMACEUTICAL PREPARATION CONTAINING THESE PYRROLIDINE | |
| CH627458A5 (en) | METHOD FOR PRODUCING NEW PIPERAZINE DERIVATIVES. | |
| DE844897C (en) | Process for the preparation of diamidine derivatives | |
| AT219025B (en) | Process for the preparation of new (2-ethyl-3,3-diphenyl-propanol-3) - and [2-ethyl-3,3-diphenyl-propen (2) -yl] -amines and their salts | |
| AT217025B (en) | Process for the preparation of new α-aminoisobutyrophenone compounds and their acid addition salts | |
| AT238183B (en) | Process for the preparation of new pyrrolidine compounds | |
| DD292908A5 (en) | PROCESS FOR THE PREPARATION OF THIENYLESSIGSAEED DERIVATIVES | |
| CH509309A (en) | 1-3-methyl-piperidino-methyl-isatin-3-thiosemicarbazone | |
| AT232500B (en) | Process for the preparation of new phenylalanine derivatives |