DE126196C - - Google Patents
Info
- Publication number
- DE126196C DE126196C DE1900126196D DE126196DA DE126196C DE 126196 C DE126196 C DE 126196C DE 1900126196 D DE1900126196 D DE 1900126196D DE 126196D A DE126196D A DE 126196DA DE 126196 C DE126196 C DE 126196C
- Authority
- DE
- Germany
- Prior art keywords
- camphidone
- camphor
- imide
- sulfuric acid
- camphidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 241000723346 Cinnamomum camphora Species 0.000 claims description 4
- 229960000846 camphor Drugs 0.000 claims description 4
- 229930008380 camphor Natural products 0.000 claims description 4
- -1 camphor imide Chemical class 0.000 claims description 4
- CHRAJVQLWOMYQI-SCZZXKLOSA-N (1s,5r)-5,8,8-trimethyl-3-azabicyclo[3.2.1]octane Chemical compound C1NC[C@H]2CC[C@]1(C)C2(C)C CHRAJVQLWOMYQI-SCZZXKLOSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 239000000047 product Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/24—Camphidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
- M 126196 KLASSE 12/?.- M 126196 CLASS 12 / ?.
. Durch elektrolytische Reduction von Camphersäureimid C10 UT15 N0.2 erhält man einen sauerstoffarmeren und wasserstoffreicheren, Camphidon genannten Körper der Zusammensetzung C10H17NO1. . By electrolytic reduction of camphor imide C 10 UT 15 N0. 2 , a body with the composition C 10 H 17 NO 1 is obtained which is less oxygenated and more hydrogen-rich, called camphidone .
Die Reaction verläuft analog der Bildung von Pyrrolidon aus Succinimid, und wie hierbei durch weitergehende Reduction gleichzeitig etwas Pyrrolidin entsteht, so bildet sich auch aus Camphersäureimid neben dem Camphidon ein noch höher hydrirter Körper, das Camphidin. The reaction proceeds analogously to the formation of pyrrolidone from succinimide, and as here by further reduction, some pyrrolidine is formed at the same time, it is also formed from camphor imide, in addition to camphidone, an even more highly hydrated body, camphidine.
Zur Darstellung dieser neuen Producte, welche wegen ihrer campherartigen Wirkungen pharmazeutische Verwendung finden · sollen, verfährt man zweckmä'fsig wie folgt:To illustrate these new products, which because of their camphor-like effects to find pharmaceutical use, one proceeds appropriately as follows:
ι kg Camphersäureimid wird mit 65 pCt. Schwefelsäure zu 10 1 gelöst und in den Kathodenraum einer elektrolytischen Zelle gefüllt. Der Anodenraum wird gleichfalls mit verdünntet Schwefelsäure beschickt. Man läfst nun etwa 3Y2 Stunden den Strom einwirken mit einer Concentration von 120 Ampere pro Liter und 10 qdm Kathodenfläche pro Liter, indem man eine nach der von Tafel (Ber. d. d. ehem. Ges. XXXIII, 2209) angegebenen Methode präparirte Bleikathode verwendet.ι kg camphor imide is 65 pCt. Sulfuric acid dissolved to 10 1 and filled into the cathode compartment of an electrolytic cell. The anode compartment is also charged with dilute sulfuric acid. Referring now to läfst about 3Y 2 hours the current act with a concentration of 120 amps per liter and 10 qdm cathode area per liter, by using a method described by panel (Ber dd former.. Ges. XXXIII, 2209) method specified präparirte lead cathode.
Nach beendeter Reduction wird der gröfste Theil der Schwefelsäure durch Calciumcarbonat entfernt und aus dem sauren Filtrate das Camphidon durch wiederholtes Ausschütteln mit Chloroform gewonnen. Nach dem Verdampfen des letzteren hinterbleibt das Camphidon als weiche Krystallmasse von schwachem campherähnlichen Geruch.When the reduction is complete, the greater part of the sulfuric acid is replaced by calcium carbonate removed and from the acidic filtrate the camphidone by repeated shaking obtained with chloroform. After the latter has evaporated, the camphidone remains as a soft crystalline mass with a faint camphor-like odor.
Der Schmelzpunkt liegt bei 220°; es sublimirt bei höherer Temperatur und siedet bei ca. 308 °.The melting point is 220 °; it sublimates at a higher temperature and boils at about 308 °.
Der Geschmack der Substanz ist kühlend und stark bitter; sie ist in allen, üblichen Lösungsmitteln, mit Ausnahme von kaltem Wasser, sehr leicht löslich. Mit wenig Wasser erwärmt schmilzt das Camphidon, löst sich reichlich darin auf und krystallisirt beim Erkalten aus.The taste of the substance is cooling and strongly bitter; it is in all, usual Solvents, with the exception of cold water, very easily soluble. With little water When warmed, the camphidone melts, dissolves in it abundantly, and crystallizes on cooling the end.
Charakteristisch ist das Pikrat, welches auf Zusatz von Pikrinlösung zur kalten wässerigen Camphidonlösung in gelben Nadeln erhalten wird.It is characterized by the picrate, which is added to the cold aqueous solution when picrine solution is added Camphidone solution is obtained in yellow needles.
Aus der schwefelsauren, von Camphidon befreiten Lösung wird nach Uebersättigen mit Alkali durch Abtreiben mit Wasserdampf das Camphidin, eine leichte weiche Krystallmasse von intensivem campherartigen Gerüche gewonnen. Seine Zusammensetzung entspricht der Formel C10 H19 N; es schmilzt scharf bei 188° zu einer farblosen Flüssigkeit und destillirt bei 209° unzersetzt. Der Körper löst sich in kaltem und heifsem Wasser recht schwer und zeichnet sich vor dem Camphidon durch seine grofse Flüchtigkeit mit Wasserdämpfen und seine starke Basicität aus.Camphidine, a light, soft crystalline mass with an intense camphor-like smell, is obtained from the sulfuric acid solution freed from camphidone after being oversaturated with alkali by stripping it with steam. Its composition corresponds to the formula C 10 H 19 N; it melts sharply at 188 ° to a colorless liquid, and distills undecomposed at 209 °. The body dissolves with great difficulty in cold and hot water, and is distinguished from camphidon by its great volatility with water vapors and its strong basicity.
Claims (1)
Verfahren zur Darstellung von Camphidon und Camphidin durch elektrolytische Reduction des Camphersäureimids in saurer Lösung.Patent claim:
Process for the preparation of camphidone and camphidine by electrolytic reduction of camphor imide in acidic solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT10016D AT10016B (en) | 1900-09-17 | 1901-12-12 | Process for the preparation of champhidon and camphidine. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE126196C true DE126196C (en) |
Family
ID=394869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1900126196D Expired - Lifetime DE126196C (en) | 1900-09-17 | 1900-09-17 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE126196C (en) |
-
1900
- 1900-09-17 DE DE1900126196D patent/DE126196C/de not_active Expired - Lifetime
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