Sodium Iodide → (4-Cyano-4-(3-cyano-5-thienyl)-5-methylhexyl]-4-[2-(4-cyanophenoxy)ethyl]piperazine

HRID 1071647노트

반응식

HRID 1071647 반응식
[C:1]([C:3]([C:11]1[S:15][CH:14]=[C:13]([C:16]#[N:17])[CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]O)#[N:2].S(Cl)(C)(=O)=O.[C:23]([C:25]1[CH:39]=[CH:38][C:28]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:27][CH:26]=1)#[N:24].[I-].[Na+]>C(#N)C.CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C.O>[C:1]([C:3]([C:11]1[S:15][CH:14]=[C:13]([C:16]#[N:17])[CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6][N:35]1[CH2:34][CH2:33][N:32]([CH2:31][CH2:30][O:29][C:28]2[CH:38]=[CH:39][C:25]([C:23]#[N:24])=[CH:26][CH:27]=2)[CH2:37][CH2:36]1)#[N:2]

참가 물질

10

반응물 4

HCID 5238Sodium IodideHCID 31297Methanesulfonyl chlorideHCID 223935934-Cyano-4-(3-cyano-5-thienyl)-5-methylhexanolHCID 223936791-[2-(4-Cyanophenoxy)ethyl]piperazine

생성물 1

HCID 22393758(4-Cyano-4-(3-cyano-5-thienyl)-5-methylhexyl]-4-[2-(4-cyanophenoxy)ethyl]piperazine수율 37.2%

시약·촉매·용매 5

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 6342Acetonitrile용매HCID 8471Triethylamine용매2회HCID 8857Ethyl Acetate용매

실험 절차

In acetonitrile (5 ml) was dissolved 4-cyano-4-(3-cyano-5-thienyl)-5-methylhexanol (0.13 g). To the mixture were added triethylamine (0.21 ml) and mesyl chloride (0.048 ml), followed by stirring at room temperature for one hour. Water was added thereto, and the mixture was extracted with ethyl acetate and further washed with brine. After drying over anhydrous magnesium sulfate, the mixture was evaporated, to give a pale yellow oil. The resulting oil was dissolved in DMF (2 ml), followed by adding a DMF solution (4 ml) of 1-[2-(4-cyanophenoxy)ethyl]piperazine (0.14 g), triethylamine (0.21 ml) and sodium iodide (0.15 g). After stirring at 60° C. overnight, ethyl acetate was added thereto, and the mixture was washed with water and further brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by NH silica gel column chromatography (hexane/ethyl acetate system), to give the title compound as a pale yellow oil (0.09 g, 33%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washfurther washed with brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe mixture was evaporated
  5. customto give a pale yellow oil
  6. stirringAfter stirring at 60° C. overnight
  7. washthe mixture was washed with water and further brine
  8. dry with materialAfter drying over anhydrous magnesium sulfate
  9. customthe solvent was evaporated
  10. customthe resulting residue was purified by NH silica gel column chromatography (hexane/ethyl acetate system)

출처 및 근거

ORD 기록
ord-4d195a5ff7204840bdd089081016b545
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906072B1

반응 노트

불러오는 중…