Sodium Iodide → 1-(p-Nitrobenzyloxycarbonyl)-4-iodopiperidine

HRID 1252212Notes

Reaction equation

HRID 1252212 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[I-:31].[Na+]>CC(C)=O>[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([I:31])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 132927101-(p-Nitrobenzyloxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Product 1

HCID 132927111-(p-Nitrobenzyloxycarbonyl)-4-iodopiperidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(p-nitrobenzyloxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine (14.78 g) in acetone (222 ml) and sodium iodide (12.71 g) was refluxed for 23 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was diluted with ethyl acetate and the extract was washed successively with aqueous 10% sodium sulfite and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and evaporated to give 1-(p-nitrobenzyloxycarbonyl)-4-iodopiperidine.

Workup

  1. temperaturewas refluxed for 23 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. additionThe residue was diluted with ethyl acetate
  5. washthe extract was washed successively with aqueous 10% sodium sulfite and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-3e23f78b9b4d4d74976465ace1163db4
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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