CH96827A - A process for the manufacture of normal butyl diethyl-β-amino-ethyl-p-aminobenzoate. - Google Patents
A process for the manufacture of normal butyl diethyl-β-amino-ethyl-p-aminobenzoate.Info
- Publication number
- CH96827A CH96827A CH96827DA CH96827A CH 96827 A CH96827 A CH 96827A CH 96827D A CH96827D A CH 96827DA CH 96827 A CH96827 A CH 96827A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- ethyl
- manufacture
- normal butyl
- aminobenzoate
- Prior art date
Links
- -1 butyl diethyl-β-amino-ethyl-p-aminobenzoate Chemical compound 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé pour la fabrication du diéthyl-p-amino-éthyl-p-aminobenzoate de butyle normal. La présente invention concerne un pro cédé pour la fabrication du di6thyl-fl-amino- éthyl-p-aminobenzoate de butyle normal de la formule (C2Hl)2 N CH2CH2 NH C'H' C00 C'H9.
Selon ce procédé on fait réagir.le fi-chlor- éthyl-diéthylamine de la formule: <B>Cl</B> CH2CH2 <B>N</B> (C2H5)2 sur l'éther N-Butylique de l'acide para- amino-benzoïque, obtenu par exemple d'après le brevet suisse no 90590.
Ces deux corps se combinent en effet par simple chauffage de leur mélange molécu laire, en donnant lieu au mono-chlorhydrate de l'éther butylique de l'acide diéthyl-p- a.mino-éthyl-para.-.amino-benzoïque, suivant l'équation (C2HII)2 N CH2CH7 Cl -f- NH2 C H- C00 C'H - (C'H')\ N CH'CH' NH C H" C00 C'H + HCl.
On arrive au même résultat en faisant réagir les deux ingrédients en solution dans un .solvant indifférent. Pour isoler l'éther- base du mono-chlorhydrate, il suffit d'ajouter à la solution aqueuse de ce dernier la quantité théorique d'un alcali.
<I>Exemple:</I> On mélange 37 grammes de para-amino- benzoate de butyle normal et 28 grammes de ,8-chloréthyldiéthylamine, et on chauffe à 115 C. pendant une heure. La masse blanche qui se forme par refroidissement est dissoute dans l'.eau froide. En ajoutant de la soude, on précipite l'éther-base, sous forme d'une huile que l'on soumet à la distillation sous pression réduite. La fraction principale passe à 214' C. sous 6 mm de mercure; c'est le cliéthyl - fl - amino-éthyl,para-amino-benzo,ate de butyle normal.
Pour transformer cette base en son monochlorhydrate on la dissout dans la quantité théorique d'acide chlor hydrique étendu, ,et on évapore cette solution à sec. En recristallisant le résidu dans l'acé tone, on obtient des aiguilles incolores fon- ,dant à 127 C., et se dissolvant dans l'eau avec réaction neutre.
C'est le monochlorhydrate de diéthyl-p- amino-éthyl-para-amino-benzoate de butyle normal, .qui, en solution aqueuse, peut être employé en thérapeutique comme anesthésiant local.
A process for the manufacture of normal butyl diethyl-p-amino-ethyl-p-aminobenzoate. The present invention relates to a process for the manufacture of normal butyl di6ethyl-fl-amino-ethyl-p-aminobenzoate of the formula (C2H1) 2 N CH2CH2 NH C'H 'C00 C'H9.
According to this process, the fi-chlor-ethyl-diethylamine of the formula: <B> Cl </B> CH2CH2 <B> N </B> (C2H5) 2 is reacted with N-butyl ether of para-amino-benzoic acid, obtained for example from Swiss Patent No. 90590.
These two bodies in fact combine by simple heating of their molecular mixture, giving rise to the mono-hydrochloride of the butyl ether of diethyl-p- a.mino-ethyl-para .-. Amino-benzoic acid, according to the equation (C2HII) 2 N CH2CH7 Cl -f- NH2 C H- C00 C'H - (C'H ') \ N CH'CH' NH CH "C00 C'H + HCl.
The same result is achieved by reacting the two ingredients in solution in an indifferent solvent. To isolate the ether base from the mono-hydrochloride, it suffices to add to the aqueous solution of the latter the theoretical quantity of an alkali.
<I> Example: </I> 37 grams of normal butyl para-aminobenzoate and 28 grams of, 8-chlorethyldiethylamine are mixed, and heated at 115 ° C. for one hour. The white mass which forms on cooling is dissolved in cold water. By adding sodium hydroxide, the ether-base is precipitated in the form of an oil which is subjected to distillation under reduced pressure. The main fraction increases to 214 ° C. under 6 mm of mercury; it is cliethyl - fl - amino-ethyl, para-amino-benzo, normal butyl ate.
To convert this base into its monohydrochloride, it is dissolved in the theoretical quantity of extended hydrochloric acid, and this solution is evaporated to dryness. By recrystallizing the residue from acetone, colorless needles are obtained, melting at 127 ° C., and dissolving in water with a neutral reaction.
It is normal butyl diethyl-p-amino-ethyl-para-amino-benzoate monohydrochloride, which, in aqueous solution, can be used therapeutically as a local anesthetic.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR96827X | 1919-11-15 | ||
| CH93120T | 1920-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH96827A true CH96827A (en) | 1922-11-16 |
Family
ID=25704616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH96827D CH96827A (en) | 1919-11-15 | 1920-04-13 | A process for the manufacture of normal butyl diethyl-β-amino-ethyl-p-aminobenzoate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH96827A (en) |
-
1920
- 1920-04-13 CH CH96827D patent/CH96827A/en unknown
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