Sodium Iodide → HCID 22248327, compound

HRID 914883Notes

Reaction equation

HRID 914883 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 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. stirringAfter further stirring for 1 hour at room temperature
  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-d7956b7ae03e45c5a5f64c40892411d4
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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