Sodium Iodide → 1-[4-Cyano-5-methyl-4-(2-naphthyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazine

HRID 1071646Notes

Reaction equation

HRID 1071646 reaction equation
[C:1]([C:3]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]O)#[N:2].C(N(CC)CC)C.S(Cl)(C)(=O)=O.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[F:41][C:42]1[CH:56]=[CH:55][C:45]([O:46][CH2:47][CH2:48][N:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[CH:44][CH:43]=1>C(#N)C.[Cl-].[Na+].O.O.CN(C)C=O>[C:1]([C:3]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)([CH:8]([CH3:9])[CH3:10])[CH2:4][CH2:5][CH2:6][N:52]1[CH2:53][CH2:54][N:49]([CH2:48][CH2:47][O:46][C:45]2[CH:44]=[CH:43][C:42]([F:41])=[CH:56][CH:55]=2)[CH2:50][CH2:51]1)#[N:2]

Participants

11

Reactant 6

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 8950271-[2-(4-Fluorophenoxy)ethyl]piperazineHCID 223937754-Cyano-5-methyl-4-(2-naphthyl)hexanol

Product 1

HCID 223936531-[4-Cyano-5-methyl-4-(2-naphthyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazineYield 69.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

In acetonitrile (5 ml) was dissolved 310 mg (1.16 mmol) of 4-cyano-5-methyl-4-(2-naphthyl)hexanol, followed by adding 190 μL (1.36 mmol) of triethylamine and 105 μl (1.36 mmol) of mesyl chloride. After completion of mesylation, 1.11 g (7.38 mmol) of sodium iodide, 255 mg (1.85 mmol) of potassium carbonate, 414 mg (1.85 mmol) of 1-[2-(4-fluorophenoxy) ethyl]piperazine, 5 ml of dimethylformamide and 1 ml of water were added thereto, followed by heating to 60° C. After completion of the reaction, brine was added thereto and the objective product was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give a crude product. The crude product was subjected to (NH) silica gel (eluted with ethyl acetate/hexane=2/3), to give 384 mg (0.81 mmol, 69.9%) of the title compound as a yellow syrup.

Workup

  1. additionwas added
  2. extractionthe objective product was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customto give a crude product

Sources & evidence

ORD record
ord-e76a4419ea6b47f2a9c8a9df2889489b
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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