Sodium Sulfite → HCID 18182360, compound

HRID 1359290Notes

Reaction equation

HRID 1359290 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)[N:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH2:9]([C:16]1[C:21]([I:1])=[CH:20][CH:19]=[C:18]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)[N:17]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 18182259HCID 18182259, compound

Product 1

HCID 18182360HCID 18182360, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under stirring in an ice bathe, 1.25 g of N-iodosuccinimide was added little by little to a mixture of 1.2 g of 2-benzyl-6-(4-ethoxycarbonylpiperidino)pyridine and 10 ml of N,N-dimethylformamide, followed by stirring as it was overnight. Sodium sulfite was added thereto, and the mixture was extracted with ethyl acetate-water. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 1-5% ethyl acetate/hexane, to give 1.42 g of the target compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate-water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. washeluted with 1-5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b33eaafa038743c1a3a10f49bcd2b9ed
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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