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

HRID 2053289

반응식

HRID 2053289 반응식
[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

참가 물질

10

반응물 6

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 71329Dofetilide2회HCID 27645871-(2-Chloroethoxy)-4-nitrobenzene2회HCID 6326970Selenium2회HCID 16218354N-methyl-4-nitrophenethylamine hydrochloride2회

생성물 1

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

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9bde05bad10a448691af53a030af1ca0
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326772B2

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