CH285687A - Process for the production of a heterocyclic nitrogen compound. - Google Patents
Process for the production of a heterocyclic nitrogen compound.Info
- Publication number
- CH285687A CH285687A CH285687DA CH285687A CH 285687 A CH285687 A CH 285687A CH 285687D A CH285687D A CH 285687DA CH 285687 A CH285687 A CH 285687A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- nitrogen compound
- heterocyclic nitrogen
- parts
- pyrrolidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- -1 heterocyclic nitrogen compound Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 title description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- 229940073608 benzyl chloride Drugs 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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. Die l:rfiiidung bezieht sich auf ein Ver fahren zur Herstellung von N-(ss-N'-Phenyl- N'-benzyl-ainino-ä.th;@>l)-pyrrolidin, welches da durch gekennzeichnet ist, class man. N-(ss-N'- Pherivl-aniino-äthvl)-pvrrolidin mit Benzyl- ehlorid kondensiert.
In Form ihrer Salze, insbesondere des Hy- drochlorids, oder der von ihnen abgeleiteten quaternären Ammoniumv erbindungen zeigt diese Verbindung bemerkenswerte antihista- miniseheWirksamkeit.
Im nachstehenden Beispiel liedenten die angegebenen Teile Gewichtsteile.
Beispiel: 31 Teile N-l-Chlor-ät.hyl-pyrrolidin-liyclro- chlorid werden mit einer Lösung, von 120 Tei len Anilin in 500 Teilen Alkohol 1.2 Stunden zum Sieden unter Rüekflusskühlung erhitzt. Man macht mit Natronlauge alkalisch Lind treibt das überschüssige Anilin mit Wasser dampf ab.
Das ziirückbleibencle N-(/3-N'-Phe- nyl-amino-ätliyl)-pyrrolidin wird im Vakuum fraktioniert (Kp.7 = 160 bis 165 C).'98 Teile dieser Verbindung werden in 250 Teilen 1.Oo/oiger wässeriger Natronlaugeiinter gutem Rühren bei 50 bis 60 C mit 65 Teilen Ben- zylehlorid versetzt.. Die Temperatur wird dann 7. Stunde auf 80 bis 90 C gesteigert und das Produkt aufgearbeitet. Man erzielt eine 95 /o ige Ausbeute.
Das Produkt ist ein schwach gelbes Öl. Es siedet, unter 2 mm Druck bei 197 bis 199 C. Das Chlorhydrat schmilzt bei 191 bis 195 C.
Process for the preparation of a heterocyclic nitrogen compound. The refinement relates to a process for the production of N- (ss-N'-phenyl-N'-benzyl-ainino-ä.th; @> l) -pyrrolidine, which is characterized by class man. N- (ss-N'- Pherivl-aniino-ether) -pvrrolidine condensed with benzyl chloride.
In the form of its salts, in particular of the hydrochloride, or of the quaternary ammonium compounds derived from them, this compound exhibits remarkable antihistamical activity.
In the example below, the specified parts are parts by weight.
Example: 31 parts of N-1-chloro-ethyl-pyrrolidine-liyclrochloride are heated to boiling with reflux cooling for 1.2 hours with a solution of 120 parts of aniline in 500 parts of alcohol. Make alkaline with sodium hydroxide solution and drive off the excess aniline with water vapor.
The remaining N - (/ 3-N'-phenyl-amino-ethyl) -pyrrolidine is fractionated in vacuo (boiling point 7 = 160 to 165 ° C.). 98 parts of this compound are dissolved in 250 parts of 10% 65 parts of benzyl chloride are added to aqueous sodium hydroxide solution while stirring well at 50 to 60 ° C. The temperature is then increased to 80 to 90 ° C. for the 7th hour and the product is worked up. A 95% yield is achieved.
The product is a pale yellow oil. It boils under 2 mm pressure at 197 to 199 C. The chlorohydrate melts at 191 to 195 C.
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 |
|---|---|
| CH285687A true CH285687A (en) | 1952-09-15 |
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 Before (1)
| 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. |
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 |
|---|---|
| CH280677A (en) | 1952-01-31 |
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