BE517147A - - Google Patents
Info
- Publication number
- BE517147A BE517147A BE517147DA BE517147A BE 517147 A BE517147 A BE 517147A BE 517147D A BE517147D A BE 517147DA BE 517147 A BE517147 A BE 517147A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- omega
- formula
- alkanol
- quaternized
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000001476 alcoholic Effects 0.000 claims description 5
- 230000000875 corresponding Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 3
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- IIMIOEBMYPRQGU-UHFFFAOYSA-L Picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 30
- -1 (dimethyl-2-hydroxy-ethyl-ammonium) -ethyl-propyl oxide dibromide Chemical compound 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000000574 ganglionic Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
COMPOSES A DEUX FONCTIONS B'AMMONIUM QUATERNAIRE POSSEDANT CHACUNE UN
GROUPEMENT ALCANOL.
La présente invention est relative à des composés contenant deux fonctions d'ammonium quaternaire possédant chacune un groupement alca- nol, ainsi qu'é leur préparation. Ces composés correspondent à la formule
EMI1.1
où R = -CH3 ou -C2H5
Z = -CH 2- , -O-, -CHOH-, -N(CH3)- x = égal ou différent de y = un nombre entier compris entre 1 et 5 n = un nombre entier compris entre 1 et 3
Hal = un atome d'halogène.
Les composés de cette configuration possèdent la propriété d'inhiber la transmission ganglionnaire des excitations nerveuses. Selon la présente invention, ils peuvent être préparés par quaternisation d'un dérivé alpha,oméga- respectivement oméga,oméga'-bis(dialcoyl)-amino par un oméga-halo- géno-alc anols
EMI1.2
La quaternisation peut être exécutée par chauffage d'une solu-
<Desc/Clms Page number 2>
EMI2.1
tion alcoolique des produits de départ.
Pour les oméga-bromo-, et oméga:"iodo- alcanols, le chauffage peut se faire à la température de reflux pendant plu- sieurs heures ; les oméga-chloroalcanols la réaction doit être effectuée en tube fermé à la température de 100 à 130 C. Les diiodures s'obtiennent également par double décomposition du sel quaternaire chloré correspondant avec un iodure alcalin en milieu alcoolique.
EMI2.2
Exemple. Dibromure de l'oxyde de 2.3'-bis(diméthyl-2-hydroxy-éthyl-ammonium)- éthyl-propyle.
On chauffe à reflux pendant 4 heures 0,2 M de 2,3'-bis(diméthyl- amino)-éthyl-propyléther et 0,4 M de 2-bromo-éthanol dissous dans 100 cm3 d'alcool absolu. On évapore à sec et on reprend le résidu dans très peu d'eau. Cette solution est extraite à l'éther et la couche aqueuse est évaporée à sec au vide poussé. Le résidu est recristallisé dans 50 car d'al- cool absolu contenant 1 cm3 d'éther isopropylique. On obtient 50 g de sel quaternaire. P.F. 128 C.
Selon ce qui précide, on peut préparer des composés à deux fonctions d'ammonium quaternaire contenant chacune un groupement alcanol correspondant à la formule I, par exemple :
EMI2.3
<tb>
<tb> R <SEP> Z <SEP> x <SEP> n <SEP> Hal <SEP> Point <SEP> de
<tb> fusion
<tb>
EMI2.4
-CH3 -CH2- 1 1 2 Br 121 C
EMI2.5
<tb>
<tb> -CH3 <SEP> -CHOH- <SEP> 1 <SEP> 1 <SEP> 2 <SEP> Br <SEP> 101 C
<tb>
EMI2.6
-CH3 -CH2- 2 2 2 Br 250 C -CH,- -CH2- 2 2 2 J 2580C -CH3 -CH2 2 2 2 Cl 23800 -CH3 -CH2- 2 2 1 Br 260 C -CH3 "2' 2 2 3 Br 158c>C -C2H5 -CH2- 2 2 2 Br 255 C
EMI2.7
<tb>
<tb> -CH3 <SEP> -CH2- <SEP> 3 <SEP> 2 <SEP> 2 <SEP> Br <SEP> 175 C
<tb> -CH3 <SEP> -CH- <SEP> 3 <SEP> 3 <SEP> 2 <SEP> Br <SEP> 165 C
<tb>
EMI2.8
-CH3 -CH 2- 5 4 2 Br 200 G -CH3 -0- 2 2 2 Br 210 G -CH3 -N( CH3 )
- 2 2 2 Cl 7.lj.0 C
EMI2.9
<tb>
<tb> -CH3 <SEP> -0- <SEP> 2 <SEP> 3 <SEP> 2 <SEP> Br <SEP> 128 C
<tb>
<Desc / Clms Page number 1>
QUATERNARY AMMONIUM TWO-FUNCTION COMPOUNDS EACH
ALCANOL GROUP.
The present invention relates to compounds containing two quaternary ammonium functions each having an alkanol group, as well as their preparation. These compounds correspond to the formula
EMI1.1
where R = -CH3 or -C2H5
Z = -CH 2-, -O-, -CHOH-, -N (CH3) - x = equal to or different from y = an integer between 1 and 5 n = an integer between 1 and 3
Hal = a halogen atom.
Compounds of this configuration possess the property of inhibiting the ganglionic transmission of nervous excitations. According to the present invention, they can be prepared by quaternization of an alpha, omega-respectively omega, omega'-bis (dialkoyl) -amino derivative with an omega-halogeno-alk anols
EMI1.2
Quaternization can be carried out by heating a solu-
<Desc / Clms Page number 2>
EMI2.1
alcoholic ration of the starting materials.
For omega-bromo- and omega: "iodo-alkanols, heating can be done at reflux temperature for several hours; omega-chloroalkanols the reaction must be carried out in a closed tube at a temperature of 100 to 130 C. The diiodides are also obtained by double decomposition of the corresponding chlorinated quaternary salt with an alkali metal iodide in an alcoholic medium.
EMI2.2
Example. 2.3'-Bis (dimethyl-2-hydroxy-ethyl-ammonium) -ethyl-propyl oxide dibromide.
0.2 M of 2,3'-bis (dimethylamino) -ethyl-propyl ether and 0.4 M of 2-bromo-ethanol dissolved in 100 cm3 of absolute alcohol are heated at reflux for 4 hours. It is evaporated to dryness and the residue is taken up in very little water. This solution is extracted with ether and the aqueous layer is evaporated to dryness in a high vacuum. The residue is recrystallized from 50 μm of absolute alcohol containing 1 cm3 of isopropyl ether. 50 g of quaternary salt are obtained. P.F. 128 C.
According to the foregoing, it is possible to prepare compounds with two quaternary ammonium functions each containing an alkanol group corresponding to formula I, for example:
EMI2.3
<tb>
<tb> R <SEP> Z <SEP> x <SEP> n <SEP> Hal <SEP> Point <SEP> of
<tb> fusion
<tb>
EMI2.4
-CH3 -CH2- 1 1 2 Br 121 C
EMI2.5
<tb>
<tb> -CH3 <SEP> -CHOH- <SEP> 1 <SEP> 1 <SEP> 2 <SEP> Br <SEP> 101 C
<tb>
EMI2.6
-CH3 -CH2- 2 2 2 Br 250 C -CH, - -CH2- 2 2 2 J 2580C -CH3 -CH2 2 2 2 Cl 23800 -CH3 -CH2- 2 2 1 Br 260 C -CH3 "2 '2 2 3 Br 158c> C -C2H5 -CH2- 2 2 2 Br 255 C
EMI2.7
<tb>
<tb> -CH3 <SEP> -CH2- <SEP> 3 <SEP> 2 <SEP> 2 <SEP> Br <SEP> 175 C
<tb> -CH3 <SEP> -CH- <SEP> 3 <SEP> 3 <SEP> 2 <SEP> Br <SEP> 165 C
<tb>
EMI2.8
-CH3 -CH 2- 5 4 2 Br 200 G -CH3 -0- 2 2 2 Br 210 G -CH3 -N (CH3)
- 2 2 2 Cl 7.lj.0 C
EMI2.9
<tb>
<tb> -CH3 <SEP> -0- <SEP> 2 <SEP> 3 <SEP> 2 <SEP> Br <SEP> 128 C
<tb>
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE517147A true BE517147A (en) |
Family
ID=154132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE517147D BE517147A (en) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE517147A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2941004A (en) * | 1955-05-19 | 1960-06-14 | Pfizer & Co C | 1, 5-bis-dimethylamino-3-pentanol diethobromide |
| US3206462A (en) * | 1962-10-31 | 1965-09-14 | Dow Chemical Co | Quaternary poly(oxyalkylene)alkylbis(diethylenetriamine) compounds |
-
0
- BE BE517147D patent/BE517147A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2941004A (en) * | 1955-05-19 | 1960-06-14 | Pfizer & Co C | 1, 5-bis-dimethylamino-3-pentanol diethobromide |
| US3206462A (en) * | 1962-10-31 | 1965-09-14 | Dow Chemical Co | Quaternary poly(oxyalkylene)alkylbis(diethylenetriamine) compounds |
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