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

HRID 2216371Notes

Reaction equation

HRID 2216371 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-ethylenedioxypyrrolidin-1-yl)pyridine and 60 ml of N,N-dimethylformamide was stirred in advance in an ice bath. 5.5 g of N-iodosuccinimide was added thereto and the resultant mixture was stirred as it was at room temperature overnight. To the reaction mixture was added 10 ml of a 1 M aqueous solution of sodium thiosulfate and the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography with 5–10% ethyl acetate/hexane, to give 6.7 g of the title compound.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-938ad3f2b3c549b4a9362192758ee24b
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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