Sodium Iodide → HCID 18423104, compound

HRID 1282073Notes

Reaction equation

HRID 1282073 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[C-:23]#[N:24].[Na+].[I-].[Na+]>CN(C)C=O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:13]2[CH2:14][CH2:15][N:10]([CH2:9][C:6]3[CH:7]=[CH:8][C:3]([CH2:2][C:23]#[N:24])=[CH:4][CH:5]=3)[CH2:11][CH2:12]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 18423133HCID 18423133, compound

Product 1

HCID 18423104HCID 18423104, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-((4-chloromethylphenyl)methyl)-1-(4-fluorophenyl)piperazine (10.0 g), sodium cyanide (1.72 g) and a catalytic amount of sodium iodide in dimethylformamide (50 ml) was stirred at 70° C. for 3 hr, and poured into ice water (200 ml) and extracted with ethyl acetate (300 ml×2). The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. The obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:2) and recrystallized from ethyl acetate-hexane to give the title compound (6.50 g) as pale-yellow crystals.

Workup

  1. extractionextracted with ethyl acetate (300 ml×2)
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:2)
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1c7dd1e5cc384ee69a79edec650e6442
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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