Pyridine → N-(4-iodobenzyl)acetamide

HRID 1181594Notes

Reaction equation

HRID 1181594 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(Cl)(Cl)Cl>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:16](=[O:18])[CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 27375334-Iodobenzylamine

Product 1

HCID 23111624N-(4-iodobenzyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Iodobenzylamine (5.32 g) was dissolved in chloroform (50 ml), and, under ice-cooling, pyridine (2.76 ml) and acetic anhydride (2.58 ml) were added and the mixture was stirred for 4 hr. The reaction mixture was washed successively with water, 1N-hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2-1:3) to give the title compound (5.18 g).

Workup

  1. temperatureunder ice-cooling
  2. washThe reaction mixture was washed successively with water, 1N-hydrochloric acid, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2-1:3)

Sources & evidence

ORD record
ord-d51619f0bc904781bb7f3e4df4788d03
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

Loading…