CH143620A - Process for the preparation of a guanidine derivative. - Google Patents
Process for the preparation of a guanidine derivative.Info
- Publication number
- CH143620A CH143620A CH143620DA CH143620A CH 143620 A CH143620 A CH 143620A CH 143620D A CH143620D A CH 143620DA CH 143620 A CH143620 A CH 143620A
- Authority
- CH
- Switzerland
- Prior art keywords
- dicarboxylic acid
- diethyl ester
- acid diethyl
- preparation
- guanidine derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000002357 guanidines Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- -1 for example # Chemical compound 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 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
- C07D211/92—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Guanidinderivates. Es wurde gefunden, dass man zu einem Guanidinderivat gelangen kann, indem man a, a', y - Trimethylpiperidin - ss, <B>ss'-</B> dicarbon- säure-diäthylester, zweckmässig in Gegen wart eines Lösungsmittels, mit Cyanamid umsetzt.
Es kann bei der Ausführung des Verfahrens auch von Salzen des<I>a, a',</I> y-Tri- methylpiperidin-ss, ss'-dicarbonsäure - cliäthyl- esters und Cyanamids ausgegangen werden.
Das Guanyl -,a,<I>ä , y</I> - trimethylpiperidin- ss, ss'-dicarbonsäure-diäthylester-nitrat bildet farblose Kristalle vom Schmelzpunkt<B>162.</B> . Sowohl das Chlorhydrat, wie die freie Base sind in Wasser löslich, jenes mit neutraler, dieses mit stark alkalischer Reaktion.
Die neue Verbindung soll therapeutische Verwendung finden. <I>Beispiel:</I> 135,5 Teile Hexahydrocollidin-dicarbon- säure-diäthylester (erhalten aus Dih ydro- collidin-dicarbonsäure-diäthylester durch ka talytische Reduktion, Siedepunkt 132 bis 134')
werden in alkoholischer Lösung mit alkoholischer Salzsäure neutralisiert. Die Chlorhydratlösung wird mit 40 Teilen Cyan-- amid einige Stunden im geschlossenen Gefäss auf 150-160' erhitzt. Das Reaktionspro dukt wird vom Alkohol befreit und der Rückstand in etwas Wasser gelöst.
Auf Zu satz von konzentrierter Natriumnitratlösung fällt das Nitrat des Guanyl-a, a', y-trimethyl- piperidin - ss, <B>ss'-</B> dicarbonsäure - diäthylesters kristallinisch -ans.
- An Stelle von Äthylalkohol können für die Umsetzung andere Lösungsmittel, zum Beispiel #,Tethylallcohol oder Wasser, verwen det werden. -
Process for the preparation of a guanidine derivative. It has been found that a guanidine derivative can be obtained by adding a, a ', y - trimethylpiperidine - ss, ss'- dicarboxylic acid diethyl ester, advantageously in the presence of a solvent, with cyanamide implements.
When carrying out the process, it is also possible to start from salts of the a, a ', γ-trimethylpiperidine-ss, ss'-dicarboxylic acid diethyl ester and cyanamide.
The guanyl -, a, <I> ä, y </I> - trimethylpiperidine- ss, ss'-dicarboxylic acid diethyl ester nitrate forms colorless crystals with a melting point of <B> 162. </B>. Both the chlorohydrate and the free base are soluble in water, the one with a neutral, the other with a strongly alkaline reaction.
The new compound should find therapeutic use. <I> Example: </I> 135.5 parts of hexahydrocollidine dicarboxylic acid diethyl ester (obtained from dihydrocollidine dicarboxylic acid diethyl ester by catalytic reduction, boiling point 132 to 134 ')
are neutralized in alcoholic solution with alcoholic hydrochloric acid. The hydrochloride solution is heated with 40 parts of cyanamide in a closed vessel to 150-160 'for a few hours. The reaction product is freed from alcohol and the residue is dissolved in a little water.
With the addition of concentrated sodium nitrate solution, the nitrate of guanyl-a, a ', y-trimethylpiperidine - ss, ss'- dicarboxylic acid diethyl ester is crystalline -ans.
- Instead of ethyl alcohol, other solvents, for example #, ethyl 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 | ||
| CH143620T | 1928-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH143620A true CH143620A (en) | 1930-11-15 |
Family
ID=25714300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH143620D CH143620A (en) | 1928-07-24 | 1928-07-24 | Process for the preparation of a guanidine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH143620A (en) |
-
1928
- 1928-07-24 CH CH143620D patent/CH143620A/en unknown
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