Water → 1-[2-(5-Bromopyridin-2-yloxy)ethyl]azepane

HRID 2423579Notes

Reaction equation

HRID 2423579 reaction equation
[N:1]1([CH2:8][CH2:9][OH:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1.O>CN(C)C=O>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([O:10][CH2:9][CH2:8][N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 693532,5-DibromopyridineHCID 88615Hexahydro-1H-azepine-1-ethanol

Product 1

HCID 579340721-[2-(5-Bromopyridin-2-yloxy)ethyl]azepaneYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-azepan-1-ylethanol (5.0 g) in N,N-dimethylformamide (100 ml) was added 60% sodium hydride (1.5 g) under a nitrogen atmosphere, the solution was stirred for 1 hour at room temperature, 2,5-dibromopyridine (7.5 g) was then added thereto followed by stirring for 4.5 hours at room temperature. Water was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then 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 (9.1 g).

Workup

  1. stirringby stirring for 4.5 hours at room temperature
  2. stirringby stirring
  3. extractionthe solution was extracted with ethyl acetate
  4. washsequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-9fdb6ba9638249f79ab7692255992852
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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