CH143616A - Process for the preparation of a guanidine derivative. - Google Patents
Process for the preparation of a guanidine derivative.Info
- Publication number
- CH143616A CH143616A CH143616DA CH143616A CH 143616 A CH143616 A CH 143616A CH 143616D A CH143616D A CH 143616DA CH 143616 A CH143616 A CH 143616A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl ester
- nipecotyl
- reaction
- preparation
- acid ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002357 guanidines Chemical class 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 claims 1
- -1 nipecotyl Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ZYXLDKSWLCDHLW-UHFFFAOYSA-N ethyl 4-amino-2-(piperidine-3-carbonyl)benzoate Chemical class C(C)OC(C1=C(C=C(C=C1)N)C(C1CNCCC1)=O)=O ZYXLDKSWLCDHLW-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N ethyl ester of p-aminobenzoic acid Natural products CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Guanidinderivates. Es -wurde befunden, dass man zu einem Guanidinderivat gelangen kann, indem man INTipecotyl - p - aminobenzoesäure - äthylester, zweckmässi- in Gegenwart eines Lösun-s- mittels, mit Cyanamid umsetzt.
Es kann bei der Ausführung des Verfahrens auch von Salzen des Nipecotyl - p - aminobenzoesäure- äthy lesters und Cyanamids ausgegangen wer den.
Das Guanyl - nipecotyl - p - aminobenzoe- s < iure-äthylester-chlorhydrat bildet farblose Kristalle, die sich bei<B>116'</B> unter Ab7abe von Kristallwasser zersetzen. Sowohl das Chlorhydrat, wie auch die freie Base sind in )Vasser löslich, jenes mit neutraler. dieses mit stark alkalischer Reaktion.
Die neue Verbindung soll therapeutische Verwendung finden.
Bespiel: 101 Teile I\Tipecotyl-p-aminobenzoesä;ure- ä.thylester-chlorhydrat (weisse Kristalle vom Schmelzpunkt 261 ) werden mit 30 Teilen Cyanamid und 400 Teilen Alkohol einige Zeit im Druckgefäss auf 150-160 erhitzt. Das Reaktionsprodukt wird vom Alkohol be freit, der Rückstand in Wasser gelöst und mit konzentrierter Pottaschelösung versetzt. Es scheidet sich eine Ölschicht ab, die mit Äther tüchtig durchgeschüttelt wird.
Dabei geht etwa noch vorhandener i-mveränderter Nipecotyl - p - aminobenzoesäureäthylester in Lösung, während die Guanidinbase in Äther unlöslich ist. Sie wird in einem Gemisch von Essigester und absolutem Alkohol gelöst, die Lö5L111g wird mit geglühtem Kaliumkarbonat getrochnet und mit alkoholischer Salzsäure neutralisiert.
Nach dem Verdampfen hinter bleibt das Chlorhydrat des Guanyl-nipecotyl- p-aminobenzoesäureäthylesters als amorphe. Harzartige Masse. die in ZVasser und Alkohol sehr leicht löslich ist. Impft man die ge sättigte wässerige Lösung, so kristallisiert es alsbald in farblosen Kristallen. Sie enthal ten Kristallwasser und schmelzen bei<B>116</B> . Der @chmelzpunlit des gut kristallisierenden Pikrates beträgt 92'6 .
An Stelle von Äthylalkohol kiinnen für die Umsetzung andere Lösun-smittel, zum Beispiel lleth@-lalkohol oder Wasser, ver- tvendet werden.
Process for the preparation of a guanidine derivative. It was found that a guanidine derivative can be obtained by reacting INTipecotyl - p - aminobenzoic acid - ethyl ester, advantageously in the presence of a solvent, with cyanamide.
When carrying out the process, salts of nipecotyl - p - aminobenzoic acid ethyl ester and cyanamide can be used as a starting point.
The guanyl-nipecotyl-p-aminobenzoic acid-ethyl ester-chlorohydrate forms colorless crystals which decompose at <B> 116 '</B> with the release of crystal water. Both the chlorohydrate and the free base are soluble in water, that with neutral water. this with a strongly alkaline reaction.
The new compound should find therapeutic use.
Example: 101 parts of I \ Tipecotyl-p-aminobenzoesä; ure- Ä.thylester -chlorhydrat (white crystals with a melting point of 261) are heated for some time in a pressure vessel to 150-160 with 30 parts of cyanamide and 400 parts of alcohol. The reaction product is freed from alcohol, the residue is dissolved in water and concentrated potash solution is added. An oil layer is deposited, which is thoroughly shaken with ether.
Any i-m-modified nipecotyl-p-aminobenzoic acid ethyl ester still present goes into solution, while the guanidine base is insoluble in ether. It is dissolved in a mixture of ethyl acetate and absolute alcohol, the Lö5L111g is dried with calcined potassium carbonate and neutralized with alcoholic hydrochloric acid.
After evaporation, the hydrate of guanyl-nipecotyl-p-aminobenzoic acid ethyl ester remains as amorphous. Resin-like mass. which is very easily soluble in water and alcohol. If the saturated aqueous solution is inoculated, it soon crystallizes in colorless crystals. They contain crystal water and melt at <B> 116 </B>. The @chmelzpunlit of the well crystallizing picrate is 92'6.
Instead of ethyl alcohol, other solvents, for example methyl alcohol or water, can be used for the reaction.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH537302X | 1928-07-24 | ||
| CH143616T | 1928-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH143616A true CH143616A (en) | 1930-11-15 |
Family
ID=25714297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH143616D CH143616A (en) | 1928-07-24 | 1928-07-24 | Process for the preparation of a guanidine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH143616A (en) |
-
1928
- 1928-07-24 CH CH143616D patent/CH143616A/en unknown
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