Azepane → 1-[(3-Nitrophenyl)methyl]azepane

HRID 2236565Notes

Reaction equation

HRID 2236565 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[NH:12]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][N:12]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8119AzepaneHCID 8471TriethylamineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 7639781-[(3-Nitrophenyl)methyl]azepaneYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-nitrobenzyl bromide (10.5 g, 48.7 mmol) in methylene chloride is added azepane (5.5 mL, 48.7 mmol) and 20.0 mL (146.1 mmol) of triethylamine, and the reaction solution is heated at 60□C under N2 for 20 minutes. After evaporating to dryness, the resulting brown residue is dissolved in methylene chloride and washed twice with saturated Na2CO3 solution, and once with brine solution. After drying over Mg2SO4, the organic solution is filtered and concentrated to give 8.0 g (70.1% yield) of brown oil.

Workup

  1. temperaturethe reaction solution is heated at 60□C under N2 for 20 minutes
  2. customAfter evaporating to dryness
  3. dissolutionthe resulting brown residue is dissolved in methylene chloride
  4. washwashed twice with saturated Na2CO3 solution
  5. dry with materialAfter drying over Mg2SO4
  6. filtrationthe organic solution is filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-899373b4ba1c42f09bfccab3bb9a0aa6
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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