Sodium Iodide → 1-[2-(4-Bromophenoxy)ethyl]azepane

HRID 1433819Notes

Reaction equation

HRID 1433819 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl.Cl[CH2:13][CH2:14][N:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[I-].[Na+]>CN(C)C=O.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH2:14][N:15]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 78084-BromophenolHCID 24758Sodium hydrideHCID 24188283N-(2-chloroethyl)perhydroazepine hydrochloride

Product 1

HCID 130635441-[2-(4-Bromophenoxy)ethyl]azepaneYield 96.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 60% sodium hydride (1.6 g) in N,N-dimethylformamide (50 ml) was added 4-bromophenol (3.0 g) under a nitrogen atmosphere, the solution was stirred for 10 minutes at room temperature, then 1-(2-chloroethyl)azepane hydrochloride (4.0 g) and sodium iodide (in catalytic amounts) were sequentially added thereto followed by stirring overnight at 80° C. Water was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (5.0 g).

Workup

  1. stirringby stirring overnight at 80° C
  2. stirringby stirring
  3. extractionthe solution was extracted with ethyl acetate
  4. washsequentially washed with water and brine
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-8e829b19eca74fc380721aae8418448c
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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