Ammonium Chloride → 3-(Azepan-1-ylmethyl)aniline

Participants

Reaction Steps

To a solution of 1-(3-nitro-benzyl)-azepane (4.0 g, 17.05 mmol) in 120 mL of 20% H2O/MeOH is added 5.05 g (102.3 mmol) of fresh iron powder, 8.25 g (153.5 mmol) of NH4Cl and the reaction mixture is refluxed under N2 for 45 min. The reaction mixture is filtered through a pad of celite to give yellow solution. After evaporating to dryness, the yellow residue is dissolved in EtOAc, washed twice with saturated NaHCO3 solution. After drying over Mg2SO4, the organic solution is filtered and concentrated to give 3.12 g (89.4% yield) of yellow oil.

Provenance & Evidence