N,N'-bis[2,3-bis(acetyloxy)propyl]-5-(3-bromo-2-oxo-1-piperidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide → 5-[3-(acetyloxy)-2-oxo-1-piperidinyl]-N,N'-bis[2,3-bis(acetyloxy)propyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233071Notes

Reaction equation

HRID 233071 reaction equation
[C:1]([O:4][CH:5]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH:19](Br)[C:18]2=[O:24])[C:13]([I:25])=[C:12]([C:26]([NH:28][CH2:29][CH:30]([O:36][C:37](=[O:39])[CH3:38])[CH2:31][O:32][C:33](=[O:35])[CH3:34])=[O:27])[C:11]=1[I:40])=[O:9])(=[O:3])[CH3:2]>C(O)(=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Ag+]>[C:1]([O:4][CH:19]1[CH2:20][CH2:21][CH2:22][N:17]([C:14]2[C:13]([I:25])=[C:12]([C:26]([NH:28][CH2:29][CH:30]([O:36][C:37](=[O:39])[CH3:38])[CH2:31][O:32][C:33](=[O:35])[CH3:34])=[O:27])[C:11]([I:40])=[C:10]([C:8]([NH:7][CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:41][O:42][C:43](=[O:45])[CH3:44])=[O:9])[C:15]=2[I:16])[C:18]1=[O:24])(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 19048418N,N'-bis[2,3-bis(acetyloxy)propyl]-5-(3-bromo-2-oxo-1-piperidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

Product 1

HCID 109531845-[3-(acetyloxy)-2-oxo-1-piperidinyl]-N,N'-bis[2,3-bis(acetyloxy)propyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

Reagents, catalysts & solvents 3

HCID 11246Silver acetateCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-(3-bromo-2-oxo-1-piperidinyl)-2,4,6-triiodo-1,3-benzenedicarboxamide of example 8b (13.7 g, 13.3 mmol) in glacial acetic acid (400 ml), was added silver acetate (5.6 g, 33.5 mmol) and the mixture was refluxed for 21 hours. After cooling to room temperature, the mixture was filtered, and the filtrate concentrated in vacuo. The residue thus obtained, was redissolved in ethyl acetate (500 ml) and washed successively with water (50 ml), saturated aqueous sodium bicarbonate (3×50 ml) and saturated aqueous sodium chloride (50 ml). After drying over magnesium sulfate, the solvent was evaporated in vacuo and the crude product, that resulted, was purified by column chromatography over silica gel to obtain 5-[3-(acetyloxy)-2-oxo-1-piperidinyl]-N,N'bis[2,3-bis(acetyloxy)propyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as a white fluffy solid (10.3 g, 83% yield).

Workup

  1. temperaturethe mixture was refluxed for 21 hours
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue thus obtained
  5. washwashed successively with water (50 ml), saturated aqueous sodium bicarbonate (3×50 ml) and saturated aqueous sodium chloride (50 ml)
  6. dry with materialAfter drying over magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customthe crude product, that resulted
  9. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-3c4b37c1be444b38bbc64d45813b0d22
Source dataset
uspto-grants-1997_01
Patent number
US05591846

Reaction notes

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