CH303582A - Process for the preparation of a new furan compound. - Google Patents
Process for the preparation of a new furan compound.Info
- Publication number
- CH303582A CH303582A CH303582DA CH303582A CH 303582 A CH303582 A CH 303582A CH 303582D A CH303582D A CH 303582DA CH 303582 A CH303582 A CH 303582A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- new
- furan compound
- parts
- furyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- -1 furan compound Chemical class 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 230000033764 rhythmic process Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- 229960004279 formaldehyde Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
Description
Verfahren zur Herstellung einer neuen Furanverbindung. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines 2-(N- Ai-alkyl-alkylaminoalkyl)-fura.ns, welches da durch gekennzeichnet ist, dass man auf N- [Furyl-(2)-methyl] -2',3'-dimethoxy-phenyl- äthylamin Formaldehyd in Gegenwart eines reduzierenden Mittels einwirken lässt.
Das so erhaltene 2-[N-(2',3'-Dimethoxy- phenyläthyl) -methylaminomethyl]-furan der Formel
EMI0001.0012
ist neu und siedet bei 130-132 (0,1 mm Hg). Es besitzt eine spezifische Wirkung gegenüber Störungen des Herzrhythmus und soll als Heilmittel Verwendung finden.
Die Reaktion wird zweckmässig so vorge nommen, dass man als reduzierendes Mittel Ameisensäure verwendet. Vorteilhaft arbeitet , man bei erhöhter Temperatur.
Gegebenenfalls lässt sich auch ein Salz des N- [Furyl- (2) -methyl ] -2', 3'-dimethoxy-phenyl- äthylamins als Ausgangsstoff verwenden.
<I>Beispiel:</I> 1.3 Gewichtsteile N- [Furyl- (2)-methyl]- 2',3'-climethoxy-phenyläthylamin werden mit 3,8 Gewichtsteilen 90%iger Ameisensäure und 5,6 Gewichtsteilen 40%igem Formaldehyd während 3 Stunden auf 90-100 erwärmt.
Die gekühlte und mit 2n-Salzsättre verdünnte Lö sung wird darauf mit Äther ausgeschüttelt, abgetrennt, mit Natronlauge alkalisch ge macht und mit Äther ausgezogen. Aus dieser ätherischen Lösung lässt sich durch Trocknen und Destillieren das 2-[N-(2',3'-Dimethoxy- phenyläthyl)-methylaminomethyl]-furan vom Kp.130-132 (0,1 mm Hg) gewinnen.
Es be sitzt die Poimnel
EMI0001.0041
Das als Ausgangsstoff verwendete N-[Fu ryl-(2)-methyl]-2',3'-dimethoxy-phenyläthyl- amin kann wie folgt hergestellt werden: 8,4 Gewichtsteile ,B-(2',3'-Dimethoxy-phe- nyl-äthylamin, 5,0 Gewichtsteile Furfurol und 80 Volumteile Alkohol werden mit 5 Gewichts- teilen R.upe-Nickel bei 50 in einer Wasser stoffatmosphäre geschüttelt, bis 1 Äquivalent Wasserstoff absorbiert. ist.
Dann wird die Hydrierung abgebrochen, der Katalysator von der Lösung abfiltriert und diese im Vakuum zur Trockne verdampft. Durch Destillation im Hochvakuum wird das entstandene N-[Furyl- (2)-methy 1] -2',3'-dimethoxy-phenyläthylamin gereinigt. Es besitzt einen Siedepunkt von 135 bis 13G bei 0,1 mm Hg.
Process for the preparation of a new furan compound. The subject of the present patent is a process for the preparation of a 2- (N-Ai-alkyl-alkylaminoalkyl) -fura.ns, which is characterized by the fact that N- [furyl- (2) -methyl] -2 ', 3'-dimethoxy-phenyl-ethylamine allows formaldehyde to act in the presence of a reducing agent.
The 2- [N- (2 ', 3'-dimethoxyphenylethyl) methylaminomethyl] furan of the formula obtained in this way
EMI0001.0012
is new and boils at 130-132 (0.1 mm Hg). It has a specific effect on disorders of the heart rhythm and is said to be used as a remedy.
The reaction is expediently carried out in such a way that formic acid is used as the reducing agent. It is advantageous to work at an elevated temperature.
If necessary, a salt of N- [furyl- (2) -methyl] -2 ', 3'-dimethoxyphenylethylamine can also be used as the starting material.
<I> Example: </I> 1.3 parts by weight of N- [furyl- (2) -methyl] -2 ', 3'-climethoxy-phenylethylamine are mixed with 3.8 parts by weight of 90% formic acid and 5.6 parts by weight of 40% Formaldehyde heated to 90-100 for 3 hours.
The cooled and diluted solution with 2N salt is then extracted with ether, separated, made alkaline with sodium hydroxide solution and extracted with ether. The 2- [N- (2 ', 3'-dimethoxyphenylethyl) -methylaminomethyl] -furan of boiling point 130-132 (0.1 mm Hg) can be obtained from this ethereal solution by drying and distilling.
It is owned by the pool
EMI0001.0041
The N- [Fu ryl- (2) -methyl] -2 ', 3'-dimethoxyphenylethylamine used as starting material can be prepared as follows: 8.4 parts by weight, B- (2', 3'-dimethoxy- Phenylethylamine, 5.0 parts by weight of furfural and 80 parts by volume of alcohol are shaken with 5 parts by weight of R.upe nickel at 50 in a hydrogen atmosphere until 1 equivalent of hydrogen is absorbed.
The hydrogenation is then stopped, the catalyst is filtered off from the solution and the solution is evaporated to dryness in vacuo. The N- [furyl- (2) -methy 1] -2 ', 3'-dimethoxyphenylethylamine formed is purified by distillation in a high vacuum. It has a boiling point of 135 to 13G at 0.1 mm Hg.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2658905X | 1951-03-22 | ||
| CH303582T | 1951-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH303582A true CH303582A (en) | 1954-11-30 |
Family
ID=25734654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH303582D CH303582A (en) | 1951-03-22 | 1951-03-22 | Process for the preparation of a new furan compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH303582A (en) |
-
1951
- 1951-03-22 CH CH303582D patent/CH303582A/en unknown
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