Dimethylformamide → HCID 69759985, compound

HRID 1359354Notes

Reaction equation

HRID 1359354 reaction equation
[I:1]N1C(=O)CCC1=O.CN(C)C=O.[CH2:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]2[CH2:31][C@H:30]3[O:32][CH2:33][CH2:34][O:35][C@@H:29]3[CH2:28]2)[N:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH2:14]([C:21]1[C:26]([I:1])=[CH:25][CH:24]=[C:23]([N:27]2[CH2:28][C@H:29]3[O:35][CH2:34][CH2:33][O:32][C@@H:30]3[CH2:31]2)[N:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 69759004HCID 69759004, compound

Product 1

HCID 69759985HCID 69759985, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.04 g of N-iodosuccinimide was added little by little to a solution of 40 ml of N,N-dimethylformamide containing 4.84 g of 2-benzyl-6-[(3R,4R)-3,4-ethylenedioxypyrrolidine-1-yl]pyridine under stirring in an ice bath, followed by stirring overnight as it was. The reaction solution was poured into water, and extracted with ethyl acetate. The organic phase was successively washed with an aqueous sodium sulfite solution, water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to filtration using silica gel and crystallized from hexane/ethyl acetate, to give 5.12 g of the target compound.

Workup

  1. stirringby stirring overnight as it
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was successively washed with an aqueous sodium sulfite solution, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed
  6. filtrationThe residue was subjected to filtration
  7. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-85ea7cbd44c5481d83febda133d8cf1a
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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