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

HRID 1071647Notes

Reaction equation

HRID 1071647 reaction equation
[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]

Participants

10

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-4d195a5ff7204840bdd089081016b545
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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