Sodium Iodide → HCID 66974186, compound

HRID 559592Notes

Reaction equation

HRID 559592 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][C:3]=1[O:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.N([O-])=O.[Na+].[Na+].[I-:29]>Cl.O>[I:29][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][C:3]=1[O:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 23668193Sodium NitriteHCID 66974193HCID 66974193, compound

Product 1

HCID 66974186HCID 66974186, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-amino-3-(2-(piperidin-1-yl)ethoxy)phenyl)pyridin-2(1H)-one (0.44 g, 1.08 mmol) in conc. HCl (3 mL) at 0° C., a solution of NaNO2 (75 mg, 1.08 mmol) in H2O (2 mL) was added dropwise. After 30 min of stirring at 0° C., NaI (0.76 g, 5.07 mmol) in H2O (2 mL) was added. After being stirred at 0° C. for 30 min, the mixture was removed to room temperature and was stirred at room temperature for 4 h. The solution was basified with 5 N NaOH to pH 10-12. The product was extracted with EtOAc, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 1-(4-iodo-3-(2-(piperidin-1-yl)ethoxy)phenyl)pyridin-2(1H)-one (116 mg).

Workup

  1. stirringAfter being stirred at 0° C. for 30 min
  2. customthe mixture was removed to room temperature
  3. stirringwas stirred at room temperature for 4 h
  4. extractionThe product was extracted with EtOAc
  5. washwashed with 5% NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-424c025ac6e14a00bc2cd8f73da59008
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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