CS226943B1 - Bis (2-dimethylaminoethyl)alkylamines and method of preparing same - Google Patents
Bis (2-dimethylaminoethyl)alkylamines and method of preparing same Download PDFInfo
- Publication number
- CS226943B1 CS226943B1 CS556282A CS556282A CS226943B1 CS 226943 B1 CS226943 B1 CS 226943B1 CS 556282 A CS556282 A CS 556282A CS 556282 A CS556282 A CS 556282A CS 226943 B1 CS226943 B1 CS 226943B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- bis
- alkylamines
- dimethylaminoethyl
- preparing same
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 7
- 150000003973 alkyl amines Chemical class 0.000 title claims description 6
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 title claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 Bis (2-dimethylaminoethyl) nonylamine Chemical compound 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JGFWIGNILMIBMV-UHFFFAOYSA-N n'-(2-aminoethyl)-n'-pentadecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCN(CCN)CCN JGFWIGNILMIBMV-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká bis( 2-dimetylaminoetyl )alkylamínov všeobecného vzorca (CH3)2N-(CH2)2-N-(CH2)2-N(CH3)2 The present invention relates to bis (2-dimethylaminoethyl) alkylamines of formula (CH 3 ) 2 N- (CH 2 ) 2 -N- (CH 2 ) 2 -N (CH 3 ) 2
R kde R značí alkylový reťazec s počtom atómov uhlíka 8 až 16 a spósobu ich přípravy.Wherein R is an alkyl chain having a number of carbon atoms of 8 to 16 and a process for their preparation.
Je známe, že bis (2-aminoetyl)amin (diety léntriamín) ale aj jeho N‘-oktyl a dodecyl deriváty majú využitie v priemysle ako aditiva do epoxidových živíc, pri výrobě různých polymérov, ako přísady do farbiacich zmesi, pohonných hmót ako chelatačné činidlá a pod.It is known that bis (2-aminoethyl) amine (diethylenetriamine) as well as its N'-octyl and dodecyl derivatives have utility in industry as additives to epoxy resins, in the production of various polymers as additives for coloring compounds, propellants as chelating agents reagents and the like.
Zo zlúčenin s vyššie uvedenou štruktúrou sú známe len deriváty, kde R = CH3, C2H5, ktoré našli využitie ako medziprodukty pri príprave biologicky účinných zlúčenin predovšetkým s ganglioblokujúcim účinkom.Of the compounds with the above structure, only derivatives are known where R = CH 3 , C 2 H 5 , which have found use as intermediates in the preparation of biologically active compounds, in particular with ganglioblocking activity.
Zlúčeniny, ktoré sú predmetom vynálezu, sú látky nové, doteraz v chemickej literatúre neopísané a slúžia ako medziprodukty v organickej syntéze pri príprave povrchovoaktívnych antimikróbne účinných zlúčenín napr. typu tris-N-oxidov bis(2-dimetylaminoetyl) alkylamínov.The compounds of the present invention are novel substances not previously described in the chemical literature and serve as intermediates in organic synthesis in the preparation of surface-active antimicrobially active compounds e.g. of the type tris-N-oxides of bis (2-dimethylaminoethyl) alkylamines.
Spósob přípravy podfa vynálezu spočíváThe process according to the invention consists of
B v reduktívnej permetylácii bis (2-aminoetyl)alkylamínov všeobecného vzorca [NH2(CH2)2]2NR, kde R značí to isté ako vyššie pomocou formaldehydu a kyseliny mravčej. Získajú sa produkty vysokej čistoty v poměrně vysokých výťažkoch.B in the reductive permethylation of bis (2-aminoethyl) alkylamines of the general formula [NH 2 (CH 2 ) 2 ] 2 NR, where R denotes the same as above with formaldehyde and formic acid. High purity products are obtained in relatively high yields.
V príkladoch, ktoré ilustrujú aleb neobmedzujú metodu přípravy, je uvedený spósob přípravy vybraných zlúčenin, ktoré sú predmetom vynálezu, a ktoré sú charakterizované svojimi fyzikálnymi konstantami.In the examples, which illustrate or do not limit the method of preparation, a method for preparing selected compounds of the invention and characterized by their physical constants is given.
Příklad 1Example 1
K 0,1 mol bis (2-aminoetyljnonylamínu sa přidá 1,6 mol kyseliny mravčej (98 %) tak, aby teplota bola 50 až 60 °C. Potom sa pomaly přidá 0,9 mol 36 %-ného vodného roztoku formaldehydu a nechá sa reagovat pri 100 °C 8 hodin. Po ochladení sa přidá 0,35 mol konc. HC1 a prchavé podiely sa odparia vo vakuu. K zvyšku sa za chladenia přidá 50 %-ný vodný roztok NaOH, kým sa neoddělí amin. Tento sa extrahuje éterom, vysuší s KOH a po oddestilovaní rozpúšťadla sa redestiluje zo sodíka.To 0.1 mol of bis (2-aminoethyl) -onylamine is added 1.6 mol of formic acid (98%) at a temperature of 50 to 60 ° C. Then 0.9 mol of a 36% aqueous formaldehyde solution is slowly added and The reaction was stirred at 100 ° C for 8 hours After cooling, 0.35 mol of conc. HCl was added and the volatiles were removed in vacuo and 50% aqueous NaOH was added to the residue while cooling until the amine separated. ether, dried with KOH and redistilled from sodium after distilling off the solvent.
Vzniká bis (2-dimetylaminoetyl) nonylamín s t. v. 172 °C/l,6 kPa; nD 20 = 1,4558; R£ (sústava aceton : 1NHC1 1 : 1, Silufol, de226943 tekcia Dragendorfovým činidlom v Muniěrovej modifikácii] — 0,80; výťažok 66 % teorie; IČ v 2761 cm-1.Bis (2-dimethylaminoethyl) nonylamine of 172 ° C / 1.6 kPa was formed; n D 20 = 1.4558; R £ (system acetone-1NHC1 1: 1, Silufol, de226943 Deprotection of the agent Dragendorfovým Muniěrovej modification] - 0.80, yield 66%; IR 2761 cm -1 in.
N—CH3N-CH3
Příklad 2Example 2
Pracovný postup je ten istý ako v příklade l s tým rozdielom, že do reakcie sa použil bis(2-aminoetyl)pentadecylamín. Vzniká his(2-dimeitylaminoetyl)pentadecylamín s t. v. 188 až 190 °C/73 Pa; nD 20 = 1,4590; R( = = 0,65; výťažok 70 % teorie; IČ vThe procedure was the same as in Example 1 except that bis (2-aminoethyl) pentadecylamine was used in the reaction. His (2-dimethylaminoethyl) pentadecylamine is formed having mp 188-190 ° C / 73 Pa; n D 20 = 1.4590; R (= 0.65; yield 70% of theory; IR in
N—CH3N-CH3
2762 cm“1.2762 cm- 1 .
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS556282A CS226943B1 (en) | 1982-07-21 | 1982-07-21 | Bis (2-dimethylaminoethyl)alkylamines and method of preparing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS556282A CS226943B1 (en) | 1982-07-21 | 1982-07-21 | Bis (2-dimethylaminoethyl)alkylamines and method of preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226943B1 true CS226943B1 (en) | 1984-04-16 |
Family
ID=5400756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS556282A CS226943B1 (en) | 1982-07-21 | 1982-07-21 | Bis (2-dimethylaminoethyl)alkylamines and method of preparing same |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS226943B1 (en) |
-
1982
- 1982-07-21 CS CS556282A patent/CS226943B1/en unknown
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