CH202181A - Process for the preparation of tropine diphenylacetate. - Google Patents
Process for the preparation of tropine diphenylacetate.Info
- Publication number
- CH202181A CH202181A CH202181DA CH202181A CH 202181 A CH202181 A CH 202181A CH 202181D A CH202181D A CH 202181DA CH 202181 A CH202181 A CH 202181A
- Authority
- CH
- Switzerland
- Prior art keywords
- tropine
- act
- allowed
- diphenylacetic acid
- diphenylacetic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- IUTYUDPWXQZWTH-YOFSQIOKSA-N [(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2,2-diphenylacetate Chemical compound C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 IUTYUDPWXQZWTH-YOFSQIOKSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 claims description 10
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 claims description 10
- QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 claims description 10
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 claims description 9
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- -1 diphenylacetic acid tropine ester Chemical class 0.000 claims 3
- YZMRCMTTYLBDPD-UHFFFAOYSA-N (2,2-diphenylacetyl) 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)OC(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 YZMRCMTTYLBDPD-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- UBUUGSRSVIYOTG-UHFFFAOYSA-N 2,2-diphenylacetyl bromide Chemical compound C1(=CC=CC=C1)C(C(=O)Br)C1=CC=CC=C1 UBUUGSRSVIYOTG-UHFFFAOYSA-N 0.000 description 1
- ZJVIZRWHJAZUNC-UHFFFAOYSA-N [I+].C[O-] Chemical compound [I+].C[O-] ZJVIZRWHJAZUNC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AORIUCNKPVHMTN-UHFFFAOYSA-N methyl 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1=CC=CC=C1 AORIUCNKPVHMTN-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Diphenylessigsäure-tropinester. Es wurde gefunden, dass man zu Diphe- nylessigsäure-tropinester gelangen kann, wenn man auf eine Verbindung, die das Radikal der Formel
EMI0001.0004
enthält, wie z. B. Diphenylessigsäure, ihre Halogenide, Ester oder ihr Anhydrid, Tropin einwirken lässt.
Der so erhaltene Diphenylessigsäure-tro- pinester bildet ein farbloses, dickflüssiges 01 vom Kp.o,oo7 168-17011, ein Hydrochlorid vom F. 206-207 , das in Wasser leicht lös lich ist, und ein Jodmethylat vom Zerset zungspunkt 252-255 .
Die neue Verbindung soll therapeutische Verwendung finden.
Beispiel; 23 Teile Diphenylessigsäurechlorid lässt man mit 14 Teilen Tropin reagieren, schüttelt das Reaktionsprodukt mit Äther und ver dünnter Salzeure, stellt die saure, wässerige Lösung alkalisch und äthert sie aus. Man trocknet diese ätherische Lösung und erhält nach dem Abdestillieren des Lösungsmittels Diphenylessigsäure-tropinester, der durch De stillation im Vakuum gereinigt werden kann.
An Stelle von Diphenylessigsäurechlorid kann auch ein anderes Halogenid, wie z. B. Diphenylessigsäurebromid, Verwendungfinden. Dieselbe Verbindung wird auch gewonnen, wenn man äquivalente Mengen Diphenyl- essigsäuremethylester und Tropin in der Wärme umsetzt und das Reaktionsprodukt im Va kuum fraktioniert destilliert. Auch andere Diphenylessigsäureester können als Ausgangs material dienen.
Man kann aber auch Diphenylessigsäure und Tropin unter Zusatz eines geeigneten Kondensationsmittels, wie z. B. Salzsäure, miteinander reagieren lassen und erhält auch so die oben beschriebene Base.
Process for the preparation of tropine diphenylacetate. It has been found that tropine diphenylacetate can be obtained by reacting to a compound which has the radical of the formula
EMI0001.0004
contains, such as B. Diphenylacetic acid, its halides, esters or its anhydride, tropine can act.
The so obtained diphenylacetic acid tropin ester forms a colorless, viscous oil of bp. oo7 168-17011, a hydrochloride of mp 206-207, which is easily soluble in water, and an iodine methoxide with decomposition point 252-255 .
The new compound should find therapeutic use.
Example; 23 parts of diphenylacetic acid chloride are allowed to react with 14 parts of tropine, the reaction product is shaken with ether and dilute salts, the acidic, aqueous solution is rendered alkaline and etherified. This ethereal solution is dried and, after the solvent has been distilled off, tropine diphenylacetate, which can be purified by distillation in vacuo.
Instead of diphenylacetic acid chloride, another halide, such as. B. diphenylacetic acid bromide, find use. The same compound is also obtained if equivalent amounts of methyl diphenylacetate and tropine are reacted in the heat and the reaction product is fractionally distilled in vacuo. Other diphenylacetic acid esters can also serve as starting material.
But you can also diphenylacetic acid and tropine with the addition of a suitable condensing agent, such as. B. hydrochloric acid, react with each other and also get the base described above.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH202181T | 1936-06-08 | ||
| CH187247T | 1936-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH202181A true CH202181A (en) | 1938-12-31 |
Family
ID=25721501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH202181D CH202181A (en) | 1936-06-08 | 1936-06-08 | Process for the preparation of tropine diphenylacetate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH202181A (en) |
-
1936
- 1936-06-08 CH CH202181D patent/CH202181A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE680662C (en) | Process for the preparation of new basic esters of diphenyl acetic acid | |
| CH194675A (en) | Process for the preparation of diphenylacetic acid pseudotropin ester. | |
| DE2011078B2 (en) | Process for purifying hexetidine | |
| CH191468A (en) | Process for the preparation of diphenylacetic acid-2-di-n-butylaminoethanol ester. | |
| DE826133C (en) | Process for the preparation of dihydroresorcinol carbamic acid esters | |
| CH191465A (en) | Process for the preparation of diphenylacetic acid-2-methylethylaminoethanol ester. | |
| CH250806A (en) | Process for the preparation of a new oxyhydrophenanthrene derivative. | |
| AT233538B (en) | Process for the preparation of new farnesyl compounds | |
| CH191467A (en) | Process for the preparation of diphenylacetic acid-2-piperidinoethanol ester. | |
| DE1468167B2 (en) | BASIC ESTERS OF BICYCLIC DICARBONIC ACIDS, THEIR ACID ADDITIONAL SALTS AND BISQUATERNAL AMMONIUM COMPOUNDS, AND PROCESS FOR THE PREPARATION OF THE SAME | |
| AT227687B (en) | Process for the preparation of basic benzoic acid esters | |
| DE724757C (en) | Process for the preparation of diazoketones | |
| CH191462A (en) | Process for the preparation of diphenylacetic acid 1-methyl-3-diethylamino-propanol ester. | |
| AT268233B (en) | Process for the preparation of new cyclopropanecarboxylic acid esters | |
| CH191461A (en) | Process for the preparation of diphenylacetic acid-2,2-dimethyl-3-diethylaminopropanol ester. | |
| CH221219A (en) | Process for the preparation of a basic ester. | |
| AT205020B (en) | Process for the preparation of new compounds of the bicycloheptane series | |
| AT210870B (en) | Process for the preparation of new halogenated 5,6-dimethylene-bicyclo- [2,2,1] -heptenen- (2) | |
| AT379375B (en) | METHOD FOR PRODUCING THE NEW 1-CHLORINE-3,5,7-TRIMETHYL-2,6-OCTADIENE | |
| CH187247A (en) | Process for the preparation of triphenylacetic acid-2-diethylaminoethanol ester. | |
| CH263037A (en) | Process for the preparation of a new derivative of 2-oxy-5-aminobenzoic acid. | |
| CH407127A (en) | Process for the preparation of N-heterocyclic compounds | |
| CH191466A (en) | Process for the preparation of diphenylacetic acid-2-diallylaminoethanol ester. | |
| DE1107241B (en) | Process for the preparation of dihydrothiophene and dihydrothiapyran-3-carboxylic acid esters | |
| CH303086A (en) | Process for the production of a coumarin derivative. |