Sodium Thiosulfate → 2-Benzyl-3-iodo-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine

HRID 1359359Notes

Reaction equation

HRID 1359359 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][CH2:17][C:16]3([O:22][CH2:21][CH2:20][O:19]3)[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:23]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[CH2:1]([C:8]1[C:13]([I:23])=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][CH2:17][C:16]3([O:19][CH2:20][CH2:21][O:22]3)[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 219422622-Benzyl-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine

Product 1

HCID 219422862-Benzyl-3-iodo-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridineYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.6 g of 2-benzyl-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridine and 60 ml of N,N-dimethylformamide was stirred in an ice bath. Into the mixture were added dropwise 5.5 g of N-iodosuccinimide, followed by stirring at room temperature overnight as it was. 10 ml of an aqueous solution containing one mol of sodium thiosulfate was added thereto, and the mixture was partitioned between ethyl acetate and water. 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 6.7 g of the target compound.

Workup

  1. stirringby stirring at room temperature overnight as it
  2. additionwas added
  3. customthe mixture was partitioned between ethyl acetate and water
  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-c8188730d63044f8a3c3dda13ba33b66
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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