MC652A1 - New amino alcohols - Google Patents
New amino alcoholsInfo
- Publication number
- MC652A1 MC652A1 MC662A MC662A MC652A1 MC 652 A1 MC652 A1 MC 652A1 MC 662 A MC662 A MC 662A MC 662 A MC662 A MC 662A MC 652 A1 MC652 A1 MC 652A1
- Authority
- MC
- Monaco
- Prior art keywords
- cyclopropyl
- amino
- amino alcohols
- new amino
- propanol
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
BREVET D'INVENTION PATENT FOR INVENTION
10 10
NOUVEAUX AMINO ALCOOLS NEW AMINO ALCOHOLS
Inventeurs : Monsieur Claude DTJFOUR Inventors: Mr. Claude DTJFOUR
et SOCIETE D'ETUDES & APPLICATIONS CHIMIQUES and SOCIETY FOR CHEMICAL STUDIES & APPLICATIONS
La présente demande de brevet d'invention concerne de nouveaux amino alcools de structure This patent application relates to novel amino alcohols with a specific structure
R-*- e"t étant une chaine carbonée R-*- e"t being a carbon chain
R * - (CH2) - OH 12 R * - (CH2) - OH 12
2 n étant égal ou supérieur à I 2n being equal to or greater than I
caractérisés par le fait que l'une au moins des chaines carbone R^ ou est constituée par un groupement cyclopropyle. characterized by the fact that at least one of the carbon chains R^ or is constituted by a cyclopropyl group.
Les produits selon l'invention qui sont doués de propriétés particulièrement intéressantes, peuvent être combinés soit à des acides pour donner des sels ou des esters, soit à des alcools ou à des phénols pour donner des ether oxydes, 15 conduisant à des molécules d'un grand intérêt The products according to the invention, which possess particularly interesting properties, can be combined either with acids to give salts or esters, or with alcohols or phenols to give ether oxides, leading to molecules of great interest.
Les produits selon l'invention peuvent être préparés à partir de 1'aminé The products according to the invention can be prepared from amine
EI-^ EI-^
D N-H D N-H
2 " 2"
20 soit par fixation d'un époxyde ou d'un cycle oxygéné selon la réaction 20 either by fixing an epoxide or an oxygenated ring according to the reaction
Rr rN-H + CH2-CH2 Rr rN-H + CH2-CH2
V V
R. R.
N — CH.-CH - R N — CH.-CH - R
25 25
R. R.
R, R,
+ 0 (CH2)n- + 0 (CH2)n-
*!• R„- *!• R„-
N — (CŒL) - OH x 2'n ff N — (CŒL) - OH x 2'n ff
L y' L y'
soit encore par condensation avec une chaine hydroxylée comportant un atome d'halogène selon le schéma or by condensation with a hydroxylated chain containing a halogen atom according to the scheme
+ X-(CH) - OH-2 n + X-(CH) - OH-2 n
■V ■V
R- R-
N N
-(ch2)n-°H -(ch2)n-°H
+ XH + XH
Parmi les produits ainsi définis l'invention concerne plus particulièrement, tant du point de vue de leur fabrication que de leur utilisation comme produits industriels nouveaux, Among the products thus defined, the invention relates more particularly, both from the point of view of their manufacture and their use as new industrial products,
Le methyl cyclopropyl amino ethanol l'ethyl cyclopropyl amino ethanol le propyl cyclopropyl amino ethanol le dicyclopropyl amino ethanol le methyl cyclopropyl amino I propanol 2 le methyl cyclopropyl amino I propanol 3 l'ethyl cyclopropyl amino I propanol 2 Methyl cyclopropyl amino ethanol ethyl cyclopropyl amino ethanol propyl cyclopropyl amino ethanol dicyclopropyl amino ethanol methyl cyclopropyl amino I propanol 2 methyl cyclopropyl amino I propanol 3 ethyl cyclopropyl amino I propanol 2
ÏL^CKj ÏL^CKj
V°2S V°2S
RrG3ïï7 RrG3ïï7
Rj=R2=cyclopropyl Rj=R2=cyclopropyl
Rt=CH^ Rt=CH^
I 3 I 3
R2=cyclopropyl n = R2=cyclopropyl n = R2=cyclopropyl n = n = R2=cyclopropyl n = R2=cyclopropyl n = R2=cyclopropyl n = n =
R2=cyclopropyl n l'ethyl cyclopropyl amino I propanol 3 le dicyclopropylamino propanol 2 le dicyclopropylamino propanol 3 le cyclopropyl methyl amino butanol le cyclopropyl ethyl amino butanol R2=cyclopropyl n ethyl cyclopropyl amino I propanol 3 dicyclopropylamino propanol 2 dicyclopropylamino propanol 3 cyclopropyl methyl amino butanol cyclopropyl ethyl amino butanol
*rCH3 *rCH3
RI=C2iï5 RI==C2H5 fiI~E2~Cycl°pr0pyl RI=C2iï5 RI==C2H5 fiI~E2~Cycl°pr0pyl
R2=cyclopropyl n = R2 = cyclopropyl n =
R2=cyclopropyl n = R2=cyclopropyl n = n = n = R2=cyclopropyl n = R2=cyclopropyl n = n = n =
Rj=R2=cyclopropyl Rj=R2=cyclopropyl
R-j-=methyl R2=cyclopropyl n - R-j-=methyl R2=cyclopropyl n -
Rj=ethyl Rj=cyclopropyl n = Rj=ethyl Rj=cyclopropyl n =
ainsi que les sels et esters de ceux-ci avec les acides minéraux ou organiques. as well as their salts and esters with mineral or organic acids.
Pour expliciter la préparation des produits selon l'invention, et sans toutefois que les précisions apportées puissent être considérées comme apportant des restrictions quant à la portée générale des procédés selon l'invention, 4 exemples de réalisation sont donnés ci-après : To explain the preparation of the products according to the invention, and without the details provided being considered as imposing restrictions on the general scope of the processes according to the invention, 4 examples of embodiments are given below:
Exemple I - Cyclopropyl methyl amino ethanol Example I - Cyclopropyl methyl amino ethanol
Dans un appareil à réaction on charge successivement 200 cm3 d'alcool et I molécule de cyclopropyl methyl aminé. On ajoute I molécule d'oxyde d'ethylène en refroidissement avec de la glace. On laisse ensuite reposer plusieurs heures, puis chauffé quelque temps à 50-60°. f In a reaction apparatus, 200 cm³ of alcohol and one molecule of cyclopropyl methylamine are successively loaded. One molecule of ethylene oxide is added while being cooled with ice. The mixture is then left to stand for several hours, and then heated for a short time at 50-60°C.
•? •?
// //
Par concentration et distillation sous vide on obtient du methyl cyclopropy-lamino ethanol avec un rendement de 80^« L e produit se présente sous forme d'une huile incolore, donnant à l'acide perchlorique untitre de 98-995-, bouillant à 140-144° à la pression atmosphérique. By concentration and vacuum distillation, methyl cyclopropy-lamino ethanol is obtained with a yield of 80%. The product is in the form of a colorless oil, giving perchloric acid a strength of 98-995%, boiling at 140-144° at atmospheric pressure.
Exemple II - Cyclopropyl methyl amino I propanol 2 Example II - Cyclopropyl methyl amino I propanol 2
En opérant de façon analogues avec de la methyl cyclopropyl aminé et de l'oxyde de propylène on obtient le produit désiré avec QT/> de rendement. By operating in a similar way with methyl cyclopropyl amine and propylene oxide, the desired product is obtained with QT/> yield.
Exemple III - Ethyl cyclopropyl amino I propanol 3 Example III - Ethyl cyclopropyl amino I propanol 3
On dissout un atome de sodium dans un excès d'alcool allylique, et on ajoute 1,2 molécule d'ethyl cyclopropyl aminé. On chauffe 2 h. à 120°o On laisse refroidir» Par traitement selon les techniques habituelles on obtient l'ethyl cyclopropyl amino I propanol 3 avec un rendement de 55 à 60fi, Chlorhydrate PF 180° (avec décomposition). One atom of sodium is dissolved in an excess of allyl alcohol, and 1.2 molecules of ethyl cyclopropyl amino are added. The mixture is heated for 2 hours at 120°C and allowed to cool. By treatment according to usual techniques, ethyl cyclopropyl amino propanol is obtained with a yield of 55 to 60 µl, hydrochloride PF 180°C (with decomposition).
Exemple IV - Dicyclopropyl amino butanol Example IV - Dicyclopropyl amino butanol
On fait réagir une molécule de chloro butanol sur deux moléculesde dicyclopro-pylamine en solution dans l'alcool, à température de reflux pendant 5 h. One molecule of chlorobutanol is reacted with two molecules of dicyclopropylamine in solution in alcohol, at reflux temperature for 5 h.
Après concentration, reprise à l'eau et traitement selon les techniques habituelles on obtient le dicyclopropyl amino butanol sous forme d'une huile épaisse jaune pale, le rendement est de 75 à 80°/o j^es produits selon l'invention donnent des sels bien cristallisés avec les acides minéraux et organiques» On prépare aisément les chlorhydrates, sulfates, oxalates, citrates, tartrates, en faisant réagir l'acide désiré sur l1amino alcool au sein d'un solvant tel que l'alcool ou l'acétone, dans les proportions moléculaireso l'es produits selon l'invention sont également susceptibles de réagir avec les acides en particulier organiques, pour donner des esters qui sont doués de propriétés très intéressantes. After concentration, recovery with water and treatment according to the usual techniques, dicyclopropyl amino butanol is obtained in the form of a thick pale yellow oil, the yield is 75 to 80%. The products according to the invention give well-crystallized salts with mineral and organic acids. Hydrochlorides, sulfates, oxalates, citrates, tartrates are easily prepared by reacting the desired acid with the amino alcohol in a solvent such as alcohol or acetone, in the molecular proportions. The products according to the invention are also capable of reacting with acids, in particular organic acids, to give esters which have very interesting properties.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MC662A MC652A1 (en) | 1966-12-06 | 1966-12-06 | New amino alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MC662A MC652A1 (en) | 1966-12-06 | 1966-12-06 | New amino alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MC652A1 true MC652A1 (en) | 1968-02-13 |
Family
ID=19737698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MC662A MC652A1 (en) | 1966-12-06 | 1966-12-06 | New amino alcohols |
Country Status (1)
| Country | Link |
|---|---|
| MC (1) | MC652A1 (en) |
-
1966
- 1966-12-06 MC MC662A patent/MC652A1/en unknown
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