CS216441B1 - N-alkyl-n,n'-dimethyl-12-ethandiamines and method of preparation the same - Google Patents

N-alkyl-n,n'-dimethyl-12-ethandiamines and method of preparation the same Download PDF

Info

Publication number
CS216441B1
CS216441B1 CS106281A CS106281A CS216441B1 CS 216441 B1 CS216441 B1 CS 216441B1 CS 106281 A CS106281 A CS 106281A CS 106281 A CS106281 A CS 106281A CS 216441 B1 CS216441 B1 CS 216441B1
Authority
CS
Czechoslovakia
Prior art keywords
dimethyl
ethanediamine
alkyl
compounds
preparation
Prior art date
Application number
CS106281A
Other languages
Czech (cs)
Slovak (sk)
Inventor
Ferdinand Devinsky
Ivan Lacko
Ludovit Krasnec
Original Assignee
Ferdinand Devinsky
Ivan Lacko
Ludovit Krasnec
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ferdinand Devinsky, Ivan Lacko, Ludovit Krasnec filed Critical Ferdinand Devinsky
Priority to CS106281A priority Critical patent/CS216441B1/en
Publication of CS216441B1 publication Critical patent/CS216441B1/en

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

yynález sa týká N-alkyl-N,N'-dimetyl-1,2-etándiatnínov všeobecného vzorca kde R značí alkylový reťazec s počtom atómov uhlika 8 až 14 a spósobu přípravy týchto zlúčenín,. ktorý spočívá v reakcii N,N'-dimetyl-1,2-etándiamínu s 1-brómalkánom v prostředísuchého benzénu alebo toluénu pri teplote varu rozpúšťadla. Finálně produkty slúžia ako východiskové látky přej oijganickú syntézu, pre přípravu biologicky účinných zlúčenín s povrchovoaktívnymi vlastnosťami.The present invention relates to N-alkyl-N, N'-dimethyl-1,2-ethanediamines formula wherein R is an alkyl chain number carbon 14 to 14 and a process for the preparation of these compounds. which consists in the reaction of N, N'-dimethyl-1,2-ethanediamine with 1-bromoalkane in dry benzene or toluene at the boiling point of the solvent. Finally, the products serve as starting materials for organic synthesis, for biological preparation active compounds with surfactant properties.

Description

Vynález sa týká N-aIkyl-N,N'-dimetyl-l,2-etándiamínov všeobecného vzorcaThe invention relates to N-alkyl-N, N'-dimethyl-1,2-ethanediamines of the general formula

R—M- CH2~ CH2-NH—CHj CHj kde R značí lineámy alkylový reťazec s počtom atómov uhlíka 8 až 14.R-N- CH 2 -CH 2 -NH-C H C H wherein R is a linear alkyl chain having a carbon number 8 to 14.

Pri príprave niektorých derivátov 1,2-etándiamínu, ktoré majú biologické, detergenčné a povrchovoaktívne vlastnosti je výhodné vychádzať z trisubstituovaného diaminu vyššie uvedeného vzorca, pretože je možné na dusík viazať rózne substituenty ovplyvňujúce vyššie uvedené vlastnosti, pričom sa získajú nesymetricky substituované terciárně aminy, ktorých příprava iným spósobom je obtiažna.In the preparation of certain 1,2-ethanediamine derivatives having biological, detergent and surface-active properties, it is preferable to start from the trisubstituted diamine of the above formula, since it is possible to bind to the nitrogen various substituents affecting the above properties to obtain unsymmetrically substituted tertiary amines. preparing in another way is difficult.

Zlúčeniny, ktoré sú predmetom vynálezu, sú nové v chemickej literatúre doteraz neopísané. Spósob přípravy, ktorý je predmetom vynálezu, vychádza z reakcie N,N'-dimetyl-l,2-etándiamínu s příslušným 1-brómalkánom v prostředí suchého benzénu alebo toluénu pri teplote varu rozpúšťadla.The compounds of the invention are novel in the chemical literature not yet described. The process of the invention is based on the reaction of N, N'-dimethyl-1,2-ethanediamine with the appropriate 1-bromoalkane in dry benzene or toluene at the boiling point of the solvent.

V príkladoch je uvedená metóda přípravy vybraných zlúčenín, ktoré sú predmetom vynálezu a ich charakterizácia. Příklady v žiadnom případe neobmedzujú rozsah použitia tejto metody.The examples show a method for preparing selected compounds of the invention and their characterization. The examples in no way limit the scope of use of this method.

Claims (2)

PREDMETSUBJECT 1. N-alkyl-N,N'-dimetyl-l,2-etándiamíny všeobecného vzorcaN-alkyl-N, N'-dimethyl-1,2-ethanediamines of the general formula R—N- CHj- C«2-NH—CHj CHj kde R značí alkylový reťazec s počtom atómov uhlíka 8 až 14.R-N-C CHj- '-NH-CH 2 CH wherein R is an alkyl chain having a carbon number 8 to 14. Příklad 1Example 1 0,25 mol N,N'-dimetyl-l,2-etándiamínu sa rozpustí v suchom beneéne a zahřeje k varu. K roztoku sa pri tejto teplote pomaly přidává 0,25 mol 1-brómnonánu v priebehu 1 hodiny. Po přidaní všetkého alkylačného činidla sa reakčná zmes zahrieva pod spatným tokom ešte 6 hodin. Po ochladení sa zmes přefiltruje, z filtrátu sa oddestiluje benzén. Zvyšok sa přečistí posobením koncentrovanej kyseliny chlorovodíkovej a uvolněním aminu z jeho amóniovej soli posobením NaOH. Po extrakcii éterom, vysušení extraktov bezvodým Na2SO4 a oddestilovaní rozpúšťadla sa produkt, ktorým je N-nonyl-N,N'-dimetyl-l,2-etándiamín předestiluje. T. v. 141 °C/1,6 kPa; n2^ = 1,4459; Rf = 0,79 (Silufol; sústava aceton : 1 N HC1 (1 : 1); detekciaDragendorfovýmčinidlom); výťažok 43 % teorie.0.25 mol of N, N'-dimethyl-1,2-ethanediamine is dissolved in dry beneene and heated to boiling. To this solution is slowly added 0.25 mol of 1-bromononane over 1 hour. After all the alkylating agent had been added, the reaction mixture was heated to reflux for 6 hours. After cooling, the mixture was filtered and benzene was distilled off from the filtrate. The residue is purified by concentration of concentrated hydrochloric acid and release of the amine from its ammonium salt by treatment with NaOH. Extraction with ether, drying with anhydrous Na 2 SO 4 and distilling off the solvent, the product, which is N-nonyl-N, N-dimethyl-l, 2-ethanediamine distilled. T. v. 141 ° C / 1.6 kPa; n 2 = 1.4459; Rf = 0.79 (Silufol, system acetone-1N HC1 (1: 1), detekciaDragendorfovýmčinidlom); yield 43% of theory. Příklad 2Example 2 Pracovný postup ako i navážky sú tie isté ako v příklade 1, do reakcie sa použil 1-brómtridekán a ako, rozpúšťadlo suchý toluén. Produkt N-tridecyl-N,N'-dimetyl-l,2-etándiámín mal t. v. 196°C/2,1 kPa; n2?, = 1,4508; Rf = 0,64; výťažok 42 % teorie.The process and the batches are the same as in Example 1, using 1-bromotridecane and dry toluene as the solvent. The product N-tridecyl-N, N'-dimethyl-1,2-ethanediamine had a melting point of 196 ° C / 2.1 kPa; n 2 ?, = 1.4508; Rf = 0.64; yield 42% of theory. Všetky zlúčeniny, ktoré sú predmetom vynálezu sa identifikovali elementámou prvkovou analýzou a spektrálnými metodami.All compounds of the invention were identified by elemental elemental analysis and spectral methods. VYNÁLEZUINVENTION 2. Spósob přípravy zlúčenín všeobecného vzorca ako v bode 1, vyznačený tým, že sa nechá reagovat’ N,N'-dimetyl-l,2-etándiamín vzorca2. A process for the preparation of compounds of the general formula as in 1, which comprises reacting N, N'-dimethyl-1,2-ethanediamine of the formula: CH3 - NH - CH2 - CH2 - NH - CH3 s 1-brómalkánom obsahujúcim v reťazci 8 až 14 atómov uhlíka v prostředí vriaceho benzénu alebo toluénu.CH 3 - NH - CH 2 - CH 2 - NH - CH 3 with 1-bromoalkane having from 8 to 14 carbon atoms in boiling benzene or toluene.
CS106281A 1981-02-16 1981-02-16 N-alkyl-n,n'-dimethyl-12-ethandiamines and method of preparation the same CS216441B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CS106281A CS216441B1 (en) 1981-02-16 1981-02-16 N-alkyl-n,n'-dimethyl-12-ethandiamines and method of preparation the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS106281A CS216441B1 (en) 1981-02-16 1981-02-16 N-alkyl-n,n'-dimethyl-12-ethandiamines and method of preparation the same

Publications (1)

Publication Number Publication Date
CS216441B1 true CS216441B1 (en) 1982-10-29

Family

ID=5344033

Family Applications (1)

Application Number Title Priority Date Filing Date
CS106281A CS216441B1 (en) 1981-02-16 1981-02-16 N-alkyl-n,n'-dimethyl-12-ethandiamines and method of preparation the same

Country Status (1)

Country Link
CS (1) CS216441B1 (en)

Similar Documents

Publication Publication Date Title
IMMEDIATA et al. β-Naphthyl derivatives of ethanolamine and n-substituted ethanolamines
KR19990013522A (en) Process for preparing substituted perhydroisoindole
US3435074A (en) Process for producing nitrodiarylamines
JPS599554B2 (en) Method for producing N-(aminoalkyl)piperazine
US2808402A (en) Method for preparing nu-sorbitylcarbamates
CS216441B1 (en) N-alkyl-n,n'-dimethyl-12-ethandiamines and method of preparation the same
KUBOTA et al. Studies on Aminobutenolide Compounds. I. The Reaction of o-Phthalaldehydic Acid with Amino Compounds
Pyman CCCXCVII.—The tautomerism of amidines. Part III. The alkylation of open-chain amidines (continued)
SU541434A3 (en) "Method for the preparation of isothiazole derivatives or their salts
US5594149A (en) Process for producing 1,3-dialkyl-2-imidazolidinone
CS47792A3 (en) Process for preparing 9-amino-1,2,3,4-tetrahydroacridine
JP2664450B2 (en) Method for producing N- (2-chlorobenzyl) -2- (2-thienyl) ethylamine
US2935524A (en) Beta-methyleneaminopropionitrile and its conversion to beta-alanine
SU1824389A1 (en) 2,4,5-trimethylbenzene-1,3-dicarbaldehyde used as intermediate product in synthesis of 2,4,5-trimethylbenzene-1,3-dinitriloxide, low-temperature curing agent for rubber-based polymer materials
US4235819A (en) Process for isolating 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds from a crude, acid reaction mixture thereof
US3517021A (en) 4-amino-3-cyanopyridines and methods of preparation
US2899429A (en) Nitroethylenes
CS216899B1 (en) N-alkyl-n,n-dimethyl-1,2-propandiamines and method of preparation thereof
JPH0115504B2 (en)
SU178759A1 (en)
Kohn et al. Bromination of Guaiacol and Debromination of Tribromoguaiacol
GB2111044A (en) Process for the production of cimetidine
KR830000025B1 (en) Chemical Degradation of Racemic Mandelic Acid
KR930002364B1 (en) Process for the preparation of tertiary succinic imido ammonium salt
James et al. Synthesis and Reactions of α-Cyanogramine1