CH470407A - Process for the preparation of hydrohalic acid salts of caffeine (8) alkylenediamines - Google Patents
Process for the preparation of hydrohalic acid salts of caffeine (8) alkylenediaminesInfo
- Publication number
- CH470407A CH470407A CH114665A CH114665A CH470407A CH 470407 A CH470407 A CH 470407A CH 114665 A CH114665 A CH 114665A CH 114665 A CH114665 A CH 114665A CH 470407 A CH470407 A CH 470407A
- Authority
- CH
- Switzerland
- Prior art keywords
- alcohol
- ether
- melting point
- crystals
- added
- Prior art date
Links
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 title claims description 21
- 150000003839 salts Chemical class 0.000 title claims description 15
- 239000002253 acid Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 11
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 title claims description 7
- 125000005263 alkylenediamine group Chemical group 0.000 title claims description 7
- 229960001948 caffeine Drugs 0.000 title claims description 7
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000013078 crystal Substances 0.000 claims description 16
- 238000002844 melting Methods 0.000 claims description 14
- 230000008018 melting Effects 0.000 claims description 14
- 230000001476 alcoholic effect Effects 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000005245 sintering Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/12—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von halogenwasserstoffsauren Salzen von Coffeino-(8)-alkylendiaminen
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung von halogenwasserstoffsauren Salzen von Coffeino-(8)-alkylendiaminen, das dadurch gekennzeichnet ist, dass man die Diamine der Einwirkung von Halogenwasserstoffsäuren unterwirft.
Es wurde gefunden, dass diesen Salzen wertvolle therapeutische Eigenschaften zukommen.
Beispiel I
Kristalle von N,N-Diäthyl-N'- Icffeino- (s)l-äthylen- diamin (Smp. 1950 C) werden in Alkohol gelöst und mit alkoholischer Salzsäure versetzt. Man fügt dann das doppelte Volumen Äther zur Lösung hinzu. Das Hydrochlorid kristallisiert aus. Sein Schmelzpunkt beträgt 2880 C, es beginnt aber schon bei 2500 C zu sintern. Die Aus beute ergibt sich zu 80%. Die Verbindung ist in Wasser sehr leicht löslich. Aus wenig heissem Alkohol und Fällen mit Äther lässt sie sich umkristallisieren.
Beispiel 2
Kristalle von N,N-Diäthyl-N' - [coffeino- (8)] -propylen- diamin mit Smp. 2200 C werden in Alkohol gelöst. Man setzt Äther hinzu und gibt langsam alkoholische Salzsäure zu, bis eine Trübung eintritt. Zunächst scheidet sich ein öl ab, welches nach kurzer Zeit kristallin erstarrt. Bei der Erhitzung der Kristallmasse tritt ab 1400 bis 1600 C Sinterung ein. Bei 1630 C wird die Masse wieder fest und schmilzt bei 2200 C. Die Ausbeute an Hydrochlorid beträgt etwa 80%.
Beispiel 3
Kristalle von N, N-Dimethyl-N'-[coffeino-(8)]-propy- lendiamin vom Smp. 1750 C werden in wenig Alkohol gelöst und die Lösung wird mit Äther versetzt. Dann erfolgt Zugabe von alkoholischer Salzsäure bis zur beginnenden Trübung. Es fällt zuerst eine öl-und gummiartige Substanz aus, die allmählich zu schönen Kristallen erstarrt. Smp. 2670 C. Nach dem Umkristallisieren aus A!Konol unct äther ernalt man das Hy(trocnloflct mit einem Smp. 2700 C. Ausbeute 75-80%.
Beispiel 4
Kristalle von N-Cyclohexyl-N'-[coffeino-(8)]-propy- lendiamin vom Smp. 1380 C werden in wenig Alkohol gelöst. Man setzt die für das Hydrochlorid berechnete Menge an alkoholischer Salzsäure zu, worauf das Salz sofort in Blättchen auskristallisiert. Smp. 2400 C. Das Salz ist in heissem Alkohol nur sehr schwer löslich, dagegen sehr leicht in Wasser. Die wässerige Lösung hat ein pH von 4.
Beispiel 5
Man löst Kristalle von N-Piperidino-N'-[coffeino-(8)]- -äthylendiamin vom Smp. 2000 C in Alkohol und setzt alkoholische Salzsäure zu. Die Ausfällung des gebildeten Hydrochlorids erfolgt durch Zugabe von Äther. : Das Salz bildet schöne, farblose Kristalle, die bei 1780 C zu sintern beginnen, sich dann wieder verfestigen, bei 2270 C nochmals erweichen und bei 2680 C unter Zersetzung schmelzen.
PATENTANSPRUCH
Verfahren zur Herstellung von halogenwasserstoffsauren Salzen von Coffeino-(8)-alkylendiaminen, dadurch gekennzeichnet, dass man die Diamine der Einwirkung von Halogenwasserstoffsäuren unterwirft.
UNTERANSPRÜCHE
1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass die Umsetzung in alkoholischer Lösung erfolgt.
2. Verfahren nach Unteranspruch 1, dadurch gekennzeichnet, dass das Produkt mit Äther ausgefällt wird.
Ludwig Merckle KG chem. pharm. Fabrik
Vertreter: Ammann & Co., Bern
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of hydrohalic acid salts of caffeine (8) alkylenediamines
The invention relates to a process for the preparation of hydrohalic acid salts of caffeine (8) alkylenediamines, which is characterized in that the diamines are subjected to the action of hydrohalic acids.
It has been found that these salts have valuable therapeutic properties.
Example I.
Crystals of N, N-diethyl-N'-Icffeino- (s) l-ethylene diamine (melting point 1950 ° C.) are dissolved in alcohol and mixed with alcoholic hydrochloric acid. Then double the volume of ether is added to the solution. The hydrochloride crystallizes out. Its melting point is 2880 C, but it starts to sinter at 2500 C. The yield is 80%. The compound is very easily soluble in water. It can be recrystallized from a little hot alcohol and cases with ether.
Example 2
Crystals of N, N-diethyl-N '- [caffeino- (8)] -propylenediamine with a melting point of 2200 ° C. are dissolved in alcohol. Ether is added and alcoholic hydrochloric acid is slowly added until it becomes cloudy. First, an oil separates out, which solidifies in a crystalline manner after a short time. When the crystal mass is heated, sintering occurs from 1400 to 1600 C. At 1630 ° C. the mass solidifies again and melts at 2200 ° C. The yield of hydrochloride is about 80%.
Example 3
Crystals of N, N-dimethyl-N '- [caffeino- (8)] - propylenediamine with a melting point of 1750 ° C. are dissolved in a little alcohol and ether is added to the solution. Then alcoholic hydrochloric acid is added until cloudiness begins. First an oil-like and gummy substance precipitates, which gradually solidifies into beautiful crystals. M.p. 2670 C. After recrystallization from alcohol and ether, the hy (trocnloflct with a melting point of 2700 C. Yield 75-80%.
Example 4
Crystals of N-cyclohexyl-N '- [caffeino- (8)] - propylenediamine with a melting point of 1380 ° C. are dissolved in a little alcohol. The amount of alcoholic hydrochloric acid calculated for the hydrochloride is added, whereupon the salt immediately crystallizes out in flakes. Mp. 2400 C. The salt is only very sparingly soluble in hot alcohol, but very easily soluble in water. The aqueous solution has a pH of 4.
Example 5
Crystals of N-piperidino-N '- [caffeino- (8)] - ethylenediamine with a melting point of 2000 ° C. are dissolved in alcohol and alcoholic hydrochloric acid is added. The hydrochloride formed is precipitated by adding ether. : The salt forms beautiful, colorless crystals that begin to sinter at 1780 C, then solidify again, soften again at 2270 C and melt at 2680 C with decomposition.
PATENT CLAIM
Process for the preparation of hydrohalic acid salts of caffeine (8) alkylenediamines, characterized in that the diamines are subjected to the action of hydrohalic acids.
SUBCLAIMS
1. The method according to claim, characterized in that the reaction takes place in alcoholic solution.
2. The method according to dependent claim 1, characterized in that the product is precipitated with ether.
Ludwig Merckle KG chem. pharm. factory
Representative: Ammann & Co., Bern
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0037317 | 1959-03-25 | ||
| CH330960A CH409974A (en) | 1959-03-25 | 1960-03-24 | Process for the preparation of new therapeutically active caffeino- (8) -alkylenediamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH470407A true CH470407A (en) | 1969-03-31 |
Family
ID=25692709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH114665A CH470407A (en) | 1959-03-25 | 1960-03-24 | Process for the preparation of hydrohalic acid salts of caffeine (8) alkylenediamines |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH470407A (en) |
-
1960
- 1960-03-24 CH CH114665A patent/CH470407A/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |