Sodium Iodide → HCID 22248327, compound

HRID 890093Notes

Reaction equation

HRID 890093 reaction equation
[O:1]1[C:5]2[C:6]([CH2:10][CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]4[C:20]([O:25]C)=[N:21][CH:22]=[CH:23][N:24]=4)[CH2:14][CH2:13]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[I-].[Na+].Cl[Si](C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[O:1]1[C:5]2[C:6]([CH2:10][CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]4[C:20](=[O:25])[NH:21][CH:22]=[CH:23][N:24]=4)[CH2:14][CH2:13]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 10340Sodium CarbonateHCID 22248142HCID 22248142, compound

Product 1

HCID 22248327HCID 22248327, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 218 mg of 3-[4-[2-(benzofuran-7-yl)ethyl]piperidino]methyl-2-methoxypyrazine in 20 ml of acetonitrile, 914 mg of sodium iodide and 0.39 ml of chlorotrimethylsilane were added while stirring on ice, and the stirring was continued for 30 minutes. After further stirring for 1 hour at 25 room temperature, ice water and aqueous sodium carbonate solution were added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water, aqueous sodium thiosulfate solution and saturated brine in that order and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, diethyl ether was added to the residue and the mixture was filtered to obtain the title compound (70 mg, 34% yield).

Workup

  1. additionwere added
  2. additionwere added to the reaction solution and extraction
  3. washThe organic layer was washed with water, aqueous sodium thiosulfate solution and saturated brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, diethyl ether
  6. additionwas added to the residue
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-76a64e9f99bf42128913c57a8e8ed1be
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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