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

HRID 2236566Notes

Reaction equation

HRID 2236566 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH2:7][N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([O-])=O.[NH4+].[Cl-]>O.CO.[Fe]>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([CH:17]=[CH:16][CH:15]=2)[NH2:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 7639781-[(3-Nitrophenyl)methyl]azepane

Product 1

HCID 64841833-(Azepan-1-ylmethyl)anilineYield 89.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

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.

Workup

  1. temperaturethe reaction mixture is refluxed under N2 for 45 min
  2. filtrationThe reaction mixture is filtered through a pad of celite
  3. customto give yellow solution
  4. customAfter evaporating to dryness
  5. dissolutionthe yellow residue is dissolved in EtOAc
  6. washwashed twice with saturated NaHCO3 solution
  7. dry with materialAfter drying over Mg2SO4
  8. filtrationthe organic solution is filtered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3b5bf613755847328487257175a7d2d1
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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