Sodium Iodide → HCID 22718343, compound

HRID 1582744Notes

Reaction equation

HRID 1582744 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)=O.[F:9][C:10]1[CH:20]=[CH:19][C:13]([O:14][CH:15](C)[CH2:16]Cl)=[CH:12][CH:11]=1.[I-].[Na+].C(N(CC)CC)C>CN(C)C=O>[F:9][C:10]1[CH:20]=[CH:19][C:13]([O:14][CH:15]([CH3:16])[CH2:1][N:3]2[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 821911-PiperazinecarboxaldehydeHCID 22718335HCID 22718335, compound

Product 1

HCID 22718343HCID 22718343, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-Formyl piperazine (2.8 g) and 2-(4-fluorophenoxy)propyl chloride (4.7 g) were dissolved in dimethylformamide (60 ml), and sodium iodide (3.2 g) and triethylamine (4.4 ml) were added thereto, and the mixture was stirred overnight at 50 to 70° C. The organic layer was partitioned by adding water and ethyl acetate, washed with brine, dried over sodium sulfate anhydrous, and evaporated. The residue was purified by Cromatorex NH silica gel column chromatography (ethyl acetate). The resulting yellow oil (12.3 g) was dissolved in methanol (20 ml), and 5N aqueous sodium hydroxide (10 ml) was added thereto and then stirred for 1 hour under reflux. The reaction mixture was evaporated, then the organic layer was partitioned by adding water and ethyl acetate, washed with brine, and dried over sodium sulfate anhydrous. The residue obtained by evaporation was purified by Cromatorex NH silica gel column chromatography (ethyl acetate/methanol system), whereby the title compound (2.2 g, 38%) was obtained as a pale yellow oil.

Workup

  1. customThe organic layer was partitioned
  2. additionby adding water and ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate anhydrous
  5. customevaporated
  6. customThe residue was purified by Cromatorex NH silica gel column chromatography (ethyl acetate)
  7. dissolutionThe resulting yellow oil (12.3 g) was dissolved in methanol (20 ml)
  8. addition5N aqueous sodium hydroxide (10 ml) was added
  9. stirringstirred for 1 hour
  10. temperatureunder reflux
  11. customThe reaction mixture was evaporated
  12. customthe organic layer was partitioned
  13. additionby adding water and ethyl acetate
  14. washwashed with brine
  15. dry with materialdried over sodium sulfate anhydrous
  16. customThe residue obtained by evaporation
  17. customwas purified by Cromatorex NH silica gel column chromatography (ethyl acetate/methanol system), whereby the title compound (2.2 g, 38%)
  18. customwas obtained as a pale yellow oil

Sources & evidence

ORD record
ord-b645f7ae931840939eb1e8b8ecaaf4d8
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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