CH309342A - A process for preparing 1,2-bis (4- (2-trimethylammonium-ethoxy) -phenyl) -3-methylbutane diiodide. - Google Patents
A process for preparing 1,2-bis (4- (2-trimethylammonium-ethoxy) -phenyl) -3-methylbutane diiodide.Info
- Publication number
- CH309342A CH309342A CH309342DA CH309342A CH 309342 A CH309342 A CH 309342A CH 309342D A CH309342D A CH 309342DA CH 309342 A CH309342 A CH 309342A
- Authority
- CH
- Switzerland
- Prior art keywords
- methylbutane
- bis
- ethoxy
- phenyl
- diiodide
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- -1 2-di-methylamino-ethoxy Chemical group 0.000 claims description 4
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 150000003385 sodium Chemical class 0.000 claims description 4
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- AXYDMXDVISXHMN-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)-3-methylbutyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C(C)C)CC1=CC=C(O)C=C1 AXYDMXDVISXHMN-UHFFFAOYSA-N 0.000 claims description 2
- 206010021118 Hypotonia Diseases 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000036640 muscle relaxation Effects 0.000 claims description 2
- 230000001766 physiological effect Effects 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- 238000001356 surgical procedure Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Procédé de préparation de diiodure de 1, 2-bis [4- (2-triméthylammonium-éthoxy)-phényl]- 3-methylbutane.
La. présente invention a pour objet la pré parution d'un compose arylaliphatique à deux fonctions éther et deux fonctions ammonium quaternaire. Ce composé, nouveau, est le diiodure de 1, 2-bis [4- (2-triméthylammonium- éthoxy)-phényl]-3-méthylbutane dont la formule est :
Selon l'invention, on fait réagir le dérivé sodé du 1, 2-bis (4-hydroxyphényl)-3-méthylbutane avec un excès de 2-diméthylaminochloréta. ne pour obtenir le 1, 2-bis [4- (2-di méthylamino-éthoxy)-phényl]-3-méthylbuta. ne et on quaternise ce composé au moyen d'un excès d'iodure de méthyle.
EMI1.1
Le composé préparé par le procédé selon
I'invention est utilisable en chirurgie à cause de ses propriétés physiologiques amenant la relaxation des muscles.
Exemple :
A une solution alcoolique de 2 moles d'éthylate de sodium, on ajoute 1 mole de 1,2-bis (4-hydroxyphényl)-3-méthylbutane (P. F.
101102 C). Après dissolution complète, on ajoute 2, 3 moles de 2-diméthylamino-chlor- éthane et on chauffe à reflux pendant 2 heures.
On laisse refroidir et on filtre le chlorure de sodium précipité. On ajoute au filtrat un excès d'acide chlorhydrique en solution dans l'éther anhydre. Le dichlorhydrate de 1,2-bis
- (2-diméthylamino-éthoxy)-phénvl]-3-mé- thylbutane précipité est filtré et dissous dans ]'eau. On libère la base au moyen de soude caustique et on l'extrait à l'éther. La solution éthérée est évaporée à sec et la. base est dissoute dans l'éthanol. On ajoute 3 moles d'iodure de méthyle et on chauffe à reflux pendant 2 heures. Après refroidissement, le diiodure quaternaire est filtré et recristallisé dans l'éthanol absolu (P. F. instant. 175 C).
REVENDICATION :
Procédé de préparation de diiodure de 1,2bis [4- (2-triméthylammonium-éthoxy)-phényl]- 3-méthylbutane, ca. ractérisé en ce que l'on fait réagir le dérivé sodé du 1, 2-bis (4-hydroxy- phényl)-3-méthylbutane avec un excès de 2-di méthylamino-chloréthane pour obtenir le 1,2bis [4- (2-dimethylamino-éthoxy)-phenyl]-3-mé- thylbutane et en ce que l'on quaternise ce composé au moyen d'un excès d'iodure de méthyle.
Le diiodure de 1, 2-bis [4-(2-triméthylammo nium-éthoxy)-phenyl]-3-méthylbutane a un point de fusion instantanée de 175 C.
**ATTENTION** fin du champ DESC peut contenir debut de CLMS **.
A process for the preparation of 1,2-bis [4- (2-trimethylammonium-ethoxy) -phenyl] - 3-methylbutane diiodide.
The present invention relates to the preparation of an arylaliphatic compound with two ether functions and two quaternary ammonium functions. This new compound is 1, 2-bis [4- (2-trimethylammonium- ethoxy) -phenyl] -3-methylbutane diiodide, the formula of which is:
According to the invention, the sodium derivative of 1, 2-bis (4-hydroxyphenyl) -3-methylbutane is reacted with an excess of 2-dimethylaminochloréta. ne to obtain 1,2-bis [4- (2-di-methylamino-ethoxy) -phenyl] -3-methylbuta. ne and this compound is quaternized with an excess of methyl iodide.
EMI1.1
The compound prepared by the process according to
The invention can be used in surgery because of its physiological properties leading to muscle relaxation.
Example:
To an alcoholic solution of 2 moles of sodium ethoxide, 1 mole of 1,2-bis (4-hydroxyphenyl) -3-methylbutane (P. F.
101102 C). After complete dissolution, 2.3 moles of 2-dimethylamino-chloroethane are added and the mixture is heated under reflux for 2 hours.
Allowed to cool and the precipitated sodium chloride filtered off. An excess of hydrochloric acid dissolved in anhydrous ether is added to the filtrate. 1,2-bis dihydrochloride
- (2-Dimethylamino-ethoxy) -phenyl] -3-methylbutane which is precipitated is filtered off and dissolved in water. The base is liberated by means of caustic soda and it is extracted with ether. The ethereal solution is evaporated to dryness and the. base is dissolved in ethanol. 3 moles of methyl iodide are added and the mixture is heated under reflux for 2 hours. After cooling, the quaternary diiodide is filtered off and recrystallized from absolute ethanol (m.p. instant. 175 C).
CLAIM:
Process for preparing 1,2bis [4- (2-trimethylammonium-ethoxy) -phenyl] - 3-methylbutane diiodide, ca. characterized in that the sodium derivative of 1, 2-bis (4-hydroxyphenyl) -3-methylbutane is reacted with an excess of 2-di-methylamino-chloroethane to give 1,2bis [4- (2 -dimethylamino-ethoxy) -phenyl] -3-methylbutane and in that this compound is quaternized by means of an excess of methyl iodide.
1,2-Bis [4- (2-trimethylammonium-ethoxy) -phenyl] -3-methylbutane diiodide has an instantaneous melting point of 175 C.
** ATTENTION ** end of DESC field can contain start of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE309342X | 1952-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH309342A true CH309342A (en) | 1955-08-31 |
Family
ID=3867540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH309342D CH309342A (en) | 1952-05-07 | 1953-05-05 | A process for preparing 1,2-bis (4- (2-trimethylammonium-ethoxy) -phenyl) -3-methylbutane diiodide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH309342A (en) |
-
1953
- 1953-05-05 CH CH309342D patent/CH309342A/en unknown
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