CH264131A - Process for the preparation of a new amine. - Google Patents
Process for the preparation of a new amine.Info
- Publication number
- CH264131A CH264131A CH264131DA CH264131A CH 264131 A CH264131 A CH 264131A CH 264131D A CH264131D A CH 264131DA CH 264131 A CH264131 A CH 264131A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- diethylamine
- tetrahydro
- ethyl
- fluoranthene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000001412 amines Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- HWEWZSACZIURKQ-UHFFFAOYSA-N 1,2,3,4-tetrahydrofluoranthene Chemical group C1=CCC(CCC2)=C3C2=C(C=CC=C2)C2=C31 HWEWZSACZIURKQ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims 3
- 230000001419 dependent effect Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- -1 sodium amide 1,2,3,4-tetrahydro-fluoranthene Chemical compound 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OWGXJHNDSSLDER-UHFFFAOYSA-N 1,2,3,3a-tetrahydrofluoranthene Chemical compound C12=CC=CC=C2C2=CC=CC3CCCC1=C32 OWGXJHNDSSLDER-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- PLOSSHSFATUNTF-UHFFFAOYSA-N [K]C1=CC=CC=C1 Chemical compound [K]C1=CC=CC=C1 PLOSSHSFATUNTF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Amins. Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines neuen Amins, das dadurch gelzennzeichnet ist, dass man eine Verbindung der Formel
EMI0001.0002
worin X einen bei der Umsetzung sieh abspal tenden Rest hqdeutet, mit einem ss-Ilalogen- ätlivl-diätlivlaniin umsetzt.
Das so erhaltene 1-(ss-Diäthylainino-äthyl)- 1,2,3,4-tetrahydro-fluoranthen siedet bei<B>1.70</B> bis 1720 unter einem Druck von 0,1 mm und bildet ein Hydrochlorid vom Schmelzpunkt 240 bis 2410.
Die neue Verbindung soll als Heilmittel Verwendung finden.
In der obigen Formel ist X zum Beispiel ein Metallatom, wie Natrium, Kalium oder Lithiuni. Man kann beispielsweise 1,2,3,4-Te- trahydro-fluoranthen in Gegenwart des ss llalogen-äthyl-diät.hylamins mit Stoffen, wie z. B. Natrium, Kalium, Lithium, Calcium oder ihren Alkoholaten, Amiden, Hydriden oder Kohlenwasserstoffverbindungen, also z.
B. mit Kalium-tert.butylat, Kalium-tert.amylat, Na triumamid, Natriumhydrid, Butyl-Lithiuin, Phenyl-Natrium oder Pheny 1-Lithium, in die entsprechende Metallverbindung überführen.
Die Umsetzung wird zweckmässig in Ge genwart, von inerten Lösungsmitteln, wie z. B. Toluol, Benzol, Xylol, Nitrobenzol, und gege benenfalls in Anwesenheit. von indifferenten Clasen, wie Stickstoff, durchgeführt.
<I>Beispiel:</I> 50 Gewichtsteile 1;2,3,4-Tetrahy dro-fhzor- anthen und 35 Gewichtsteile ss-Chlor-äthyl-di- äthy lamin werden in 20 Volumt-eilen Toluol in Gegenwart. von 12 Gewichtsteilen Natrium- amid mehrere Stunden erhitzt.
Nach beende ter Umsetzung schüttelt man die erhaltene 'foluollösung zuerst mit Wasser aus und hier auf mit verdünnter Chlorwasserstoffsäure. Dabei fällt das IIydroehlorid des 1-(ss-Di- ät.liyiamino - äthy 1) -1,2,3,4-tetrahydro-f luoran- t.hens der Formel.
EMI0001.0048
kristallin aus. Diese Verbindung lässt sich um kristallisieren und schmilzt bei 240 bis 2410.
Die freie Base bildet ein gelbes öl vom Kpo,l <B>1.70</B> bis<B>1720.</B> Von dieser Base können auch andere Salze gebildet werden, wie z. B. ein saures Sulfat vom Schmelzpunkt 168 bis<B>1700,</B> ein Nitrat vom Schmelzpunkt 158 bis 16011 und ein Phosphat, welches mit einem Mol Kri stallwasser kristallisiert tuid nach scharfem Trocknen einen Schmelzpunkt von 160 bis <B>1630</B> aufweist. Das Phosphat ist in Wasser leicht: löslich, während die andern erwähnten Salze weniger löslich sind.
Zur Herstellung der Kaliumverbindung des Tetrahydrofluoranthens kann man das Tetrahydrofluoranthen mit Phenylkalium um setzen.
Process for the preparation of a new amine. The subject of the present patent bil det a process for the preparation of a new amine which is characterized in that a compound of the formula
EMI0001.0002
where X denotes a residue that splits off during the reaction, with an ß-ilalogen-ätlivl-dietlivlaniin.
The 1- (ss-diethylainino-ethyl) - 1,2,3,4-tetrahydrofluoranthene thus obtained boils at 1.70 until 1720 under a pressure of 0.1 mm and forms a hydrochloride with a melting point 240 to 2410.
The new compound is said to be used as a remedy.
In the above formula, for example, X is a metal atom such as sodium, potassium or lithium. You can, for example, 1,2,3,4-Tetrahydro-fluoranthene in the presence of ss llalogen-ethyl-diet.hylamins with substances such as. B. sodium, potassium, lithium, calcium or their alcoholates, amides, hydrides or hydrocarbon compounds, so z.
B. with potassium tert-butoxide, potassium tert-amylate, sodium amide, sodium hydride, butyl-lithium, phenyl-sodium or phenyl-1-lithium, converted into the corresponding metal compound.
The implementation is expedient in Ge present, of inert solvents, such as. B. toluene, benzene, xylene, nitrobenzene, and if necessary in the presence. performed by indifferent clases such as nitrogen.
<I> Example: </I> 50 parts by weight of 1; 2,3,4-tetrahydro-fhzor- anthen and 35 parts by weight of β-chloro-ethyl-diethylamine are present in 20 parts by volume of toluene. heated by 12 parts by weight of sodium amide for several hours.
After the end of the reaction, the resulting 'foluene solution is first extracted with water and then on with dilute hydrochloric acid. This drops the hydrochloride of 1- (ss-diet.liyiamino-ethy 1) -1,2,3,4-tetrahydro-fluoranthene of the formula.
EMI0001.0048
crystalline. This compound can be re-crystallized and melts at 240 to 2410.
The free base forms a yellow oil from Kpo, l <B> 1.70 </B> to <B> 1720. </B> Other salts can also be formed from this base, such as e.g. B. an acid sulphate with a melting point of 168 to 1700, a nitrate with a melting point of 158 to 16011 and a phosphate which crystallizes with one mole of crystal water tuid, after thorough drying, a melting point of 160 to 1630 / B>. The phosphate is easily soluble in water, while the other salts mentioned are less soluble.
To prepare the potassium compound of tetrahydrofluoranthene you can put the tetrahydrofluoranthene with phenylpotassium.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH264131T | 1945-12-21 | ||
| CH269067T | 1947-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH264131A true CH264131A (en) | 1949-09-30 |
Family
ID=25730718
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264131D CH264131A (en) | 1945-12-21 | 1945-12-21 | Process for the preparation of a new amine. |
| CH269067D CH269067A (en) | 1945-12-21 | 1947-01-31 | Process for the preparation of a new amine. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH269067D CH269067A (en) | 1945-12-21 | 1947-01-31 | Process for the preparation of a new amine. |
Country Status (2)
| Country | Link |
|---|---|
| AT (2) | AT162911B (en) |
| CH (2) | CH264131A (en) |
-
1945
- 1945-12-21 CH CH264131D patent/CH264131A/en unknown
-
1946
- 1946-12-18 AT AT162911D patent/AT162911B/en active
-
1947
- 1947-01-31 CH CH269067D patent/CH269067A/en unknown
- 1947-12-23 AT AT165058D patent/AT165058B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CH269067A (en) | 1950-06-15 |
| AT165058B (en) | 1950-01-10 |
| AT162911B (en) | 1949-04-25 |
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