CH267633A - Process for the preparation of an ethylene diamine derivative. - Google Patents
Process for the preparation of an ethylene diamine derivative.Info
- Publication number
- CH267633A CH267633A CH267633DA CH267633A CH 267633 A CH267633 A CH 267633A CH 267633D A CH267633D A CH 267633DA CH 267633 A CH267633 A CH 267633A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethylene diamine
- preparation
- diamine derivative
- dimethylamino
- pyridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- 125000003916 ethylene diamine group Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- GEZMEIHVFSWOCA-UHFFFAOYSA-N (4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C=C1 GEZMEIHVFSWOCA-UHFFFAOYSA-N 0.000 claims description 2
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- VKMKSMCOLOJDJQ-UHFFFAOYSA-N n'-[(4-fluorophenyl)methyl]-n,n-dimethyl-n'-pyridin-2-ylethane-1,2-diamine Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=C(F)C=C1 VKMKSMCOLOJDJQ-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- -1 aromatic sulfonic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Äthylendiaminderivates. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Äthylen- dianiinderiv ates. Das Verfahren ist dadurch gekennzeichnet, dass man 2-(f Dimethylamino- äthylamino)-pyridin mit einem reaktionsfähi gen Ester des p-Fluor-benzylalkohols umsetzt..
Als reaktionsfähige Ester seien beispielsweise die Ester mit Halogenwasserstoffsäuren, ins besondere das Chlorid, Bromid und Jodid, die Ester mit. Schwefelsäure, mit aliphatischen und mit aromatischen Sulfonsäuren genannt..
Die erhaltene neue Verbindung, das N,N- Dinietliyl-N'- (p-f luor- benzyl) - N'- (2-pyridyl) - äthylendianiin, ist ein Massgelbes Öl vom Siedepunkt 132 unter 0,1 mm Druck. Ihr Hydrochlorid schmilzt bei 168 bis 170 . Die neue Verbindung soll therapeutische Verwen dung finden.
<I>Beispiel:</I> Zu einer Lösung von 16,5 Teilen 2-(ss-Di- methylamino-äthylamino)-pyridin in 75 Teilen Toluol wird eine Suspension von 4 Teilen ge- pulvertem Nat.riumamid in 10 Teilen Tolitol zufliessen gelassen. Das Gemisch wird unter gutem Rühren bis zum Aufhören der Ammo- niakentwicklung (2 bis 3 Stunden) unter Rüekflu13 zum Sieden erhitzt und dann auf ungefähr 0 abgekühlt.
Unter weiterem Rüh ren werden 16 Teile p-Fluor-benzylchlorid zutropfen gelassen, worauf wieder aufge wärmt und 15 Stunden bei 110 bis 120 Bad temperatur gerührt wird. Nach dem Abküh len wird das Reaktionsgemisch zuerst mit Wasser gewaschen, hernach die abgetrennte Toluolschicht mit verdünnter Salzsäure aus geschüttelt, der salzsaure wässerige Auszug mit gesättigter Sodalösung oder 30prozentiger Natronlauge stark alkalisch gestellt und die ausgeschiedene Base in Äther aufgenommen.
Nach Trocknen der ätherischen. Lösung mit wasserfreiem Natriumsulfat und Abdampfen des Lösungsmittels wird das erhaltene braune basische Öl im Vakuum bei 0,1 mm Druck fraktioniert; aus der Fraktion von 130 bis 140 erhält man durch nochmalige Destilla tion N,N-Dimethyl-N'-(p-fluor-benzyl)-N'-(2- pyiidyl)-äthylendiamin vom Siedepunkt 132 bei 0,1 mm Druck als blassgelbliches, viskoses Öl.
Process for the preparation of an ethylenediamine derivative. The present patent is a process for the preparation of a ethylene dianiinderiv ates. The process is characterized in that 2- (f dimethylamino-äthylamino) -pyridine is reacted with a reactive ester of p-fluoro-benzyl alcohol ..
Examples of reactive esters are the esters with hydrohalic acids, in particular the chloride, bromide and iodide, the esters with. Sulfuric acid, called with aliphatic and with aromatic sulfonic acids ..
The new compound obtained, N, N-dinietliyl-N'- (p-fluorobenzyl) -N'- (2-pyridyl) -ethylenedianiine, is a pale yellow oil with a boiling point of 132 under 0.1 mm pressure. Your hydrochloride melts at 168 to 170. The new compound is intended to find therapeutic use.
<I> Example: </I> A suspension of 4 parts of powdered sodium amide in 10 parts of tolitol is added to a solution of 16.5 parts of 2- (ß-dimethylamino-ethylamino) -pyridine in 75 parts of toluene allowed to flow. The mixture is heated to boiling under reflux while stirring well until the evolution of ammonia ceases (2 to 3 hours) and then cooled to approximately zero.
With further stirring, 16 parts of p-fluoro-benzyl chloride are added dropwise, whereupon it is warmed up again and stirred for 15 hours at 110 to 120 bath temperature. After cooling down, the reaction mixture is first washed with water, then the separated toluene layer is shaken off with dilute hydrochloric acid, the hydrochloric acid aqueous extract is made strongly alkaline with saturated soda solution or 30 percent sodium hydroxide solution and the precipitated base is taken up in ether.
After drying the essential. Solution with anhydrous sodium sulfate and evaporation of the solvent, the brown basic oil obtained is fractionated in vacuo at 0.1 mm pressure; from the fraction of 130 to 140 is obtained by repeated distillation N, N-dimethyl-N '- (p-fluoro-benzyl) -N' - (2-pyiidyl) ethylenediamine of boiling point 132 at 0.1 mm pressure as pale yellowish, viscous oil.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH267633T | 1947-08-19 | ||
| CH264754T | 1947-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267633A true CH267633A (en) | 1950-03-31 |
Family
ID=25730765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267633D CH267633A (en) | 1947-08-19 | 1947-08-19 | Process for the preparation of an ethylene diamine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267633A (en) |
-
1947
- 1947-08-19 CH CH267633D patent/CH267633A/en unknown
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