N-Iodosuccinimide → HCID 18182331, compound

HRID 1359337Notes

Reaction equation

HRID 1359337 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:19]N1C(=O)CCC1=O>CN(C)C=O>[C:1]1([C:7]2[C:12]([I:19])=[CH:11][CH:10]=[C:9]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 120273N-Iodosuccinimide2×HCID 181822434-(6-Phenyl-2-pyridinyl)morpholine

Product 1

HCID 18182331HCID 18182331, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 750 mg of 2-phenyl-6-morpholinopyridine and 5 ml of N,N-dimethylformamide was stirred in an ice bath, and to the mixture was added 740 mg of N-iodosuccinimide, followed by stirring at room temperature overnight. Further, 70 mg of N-iodosuccinimide was added thereto, followed by stirring at room temperature for 5 hours. The reaction mixture was extracted by adding ethyl acetate, water and sodium sulfite thereto, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using 5-10% ethyl acetate/hexane, to give 1.1 g of the target compound.

Workup

  1. stirringby stirring at room temperature for 5 hours
  2. extractionThe reaction mixture was extracted
  3. additionby adding ethyl acetate, water and sodium sulfite
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d4b4844bdeed4d7ab4a47c2867fe8a60
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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