Potassium Iodide → N-Methyl-2-(4-nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethanamine

HRID 2053289

Reaktionsgleichung

Reaktionsgleichung von HRID 2053289
[Se].CN(CCOC1C=CC(NS(C)(=O)=O)=CC=1)CCC1C=CC(NS(C)(=O)=O)=CC=1.Cl.[CH3:32][NH:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1.Cl[CH2:46][CH2:47][O:48][C:49]1[CH:54]=[CH:53][C:52]([N+:55]([O-:57])=[O:56])=[CH:51][CH:50]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[CH3:32][N:33]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)[CH2:46][CH2:47][O:48][C:49]1[CH:50]=[CH:51][C:52]([N+:55]([O-:57])=[O:56])=[CH:53][CH:54]=1

Komponenten

10

Edukt 6

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 71329Dofetilide2×HCID 27645871-(2-Chloroethoxy)-4-nitrobenzene2×HCID 6326970Selenium2×HCID 16218354N-methyl-4-nitrophenethylamine hydrochloride2×

Produkt 1

HCID 14645090N-Methyl-2-(4-nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In another embodiment, the competitive inhibitor is a selenium analog of dofetilide (N-[4-(2-[2-[4-(methanesulphonamido)phenoxy]-N-methylethylamino]ethyl)phenyl]methane-sulfphonamide). In one aspect of this embodiment, the selenium analog is di-seleno-dofetilide(n-[4-(2-[2-[4-(methaneselenodoioxamido)phenoxyl]-N-methylethylamino)ethyl)phenyl]-methane-selenodioxamide). Di-seleno-dofetilide may be synthesized according to the scheme shown in FIG. 3, which is based on the synthesis of dofetilide described in U.S. Pat. No. 6,124,363. First, N-methyl-2-(4-nitrophenyl)ethylamine hydrochloride (compound 310) is mixed with 4-(2-chloroethoxy)nitrobenzene (compound 320), anhydrous potassium carbonate, potassium iodide, tetra-n-butylammonium iodide and deionized water and heated under reflux for 3 hours. Next, the mixture is cooled to about 40° C., ethyl acetate is added, and the mixture is extracted with ethyl acetate and concentrated. Ethanol is then added to the extract to precipitate the product and the product is filtered to give N-Methyl-N-[2-(4-nitrophenoxy)ethyl]-4-nitrophenethylamine (compound 330). In the next step, compound 330 and 5% w/v palladium-on-carbon are added to methanol, stirred and hydrogenated at 60 p.s.i. to give N-Methyl-N-[2-(4-aminophenoxy)ethyl]-4-aminophethylamine (compound 340). Compound 340 is then added to acetonitrile, followed by triethylamine and methaneselenodioxy chloride. Sodium carbonate is then added to the reaction mixture and distilled. Next, sodium hydroxide is added to the mixture, followed by concentrated hydrochloric acid. The solid is the collected by filtration, washed with water, and dried to obtain di-seleno-dofetilide (compound 350).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. extractionthe mixture is extracted with ethyl acetate
  4. concentrationconcentrated
  5. additionEthanol is then added to the
  6. extractionextract
  7. customto precipitate the product
  8. filtrationthe product is filtered

Quellen und Nachweise

ORD-Eintrag
ord-9bde05bad10a448691af53a030af1ca0
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326772B2

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