Dimethylformamide → HCID 69758614, compound

HRID 1359366Notes

Reaction equation

HRID 1359366 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N:22]2[CH2:26][C@H:25]3[O:27][CH2:28][O:29][C@H:24]3[CH2:23]2)[N:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(C)C=O>O>[CH2:9]([C:16]1[C:21]([I:1])=[CH:20][CH:19]=[C:18]([N:22]2[CH2:23][C@H:24]3[O:29][CH2:28][O:27][C@H:25]3[CH2:26]2)[N:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 69758628HCID 69758628, compound

Product 1

HCID 69758614HCID 69758614, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

143 mg of N-iodosuccinic acid imide was added little by little to a mixture of 150 mg of 2-benzyl-6-(cis-3,4-methylenedioxypyrrolidine-1-yl)pyridine and 5.0 ml of N,N-dimethylformamide under ice-cooling, followed by stirring overnight as it was. The reaction solution was poured into water, and then extracted with ethyl acetate. The organic phase was washed with sodium thiosulfate, water and brine, and the solvent was removed. The residue was subjected to silica gel column chromatography and eluted with hexane and then with hexane/ethyl acetate (4:1), to give 116 mg of the target compound.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with sodium thiosulfate, water and brine
  4. customthe solvent was removed
  5. washeluted with hexane

Sources & evidence

ORD record
ord-c36d458be31c4ba0a81193389200001d
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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