4-Methylmorpholine → HCID 57517517, compound

HRID 2368156Notes

Reaction equation

HRID 2368156 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15].CN1CC[O:21]CC1>C(#N)C>[CH:11]1([CH2:10][O:9][C:6]2[CH:7]=[CH:8][C:3]([CH:2]=[O:21])=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 79724-MethylmorpholineHCID 57517516HCID 57517516, compound

Product 1

HCID 57517517HCID 57517517, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(bromomethyl)-4-(cyclopropylmethoxy)-2-nitrobenzene (11.4 g) in acetonitrile (200 mL) were added molecular sieves 4 Å (55 g) and N-methylmorpholine (9.37 g) at room temperature. Under an argon atmosphere, the reaction mixture was stirred at room temperature for 1 hr, and filtered through celite. The obtained filtrate was concentrated under reduced pressure, and the residue was dissolved in diethyl ether and the solution was washed twice with 6N hydrochloric acid and once with water. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (6.39 g).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe obtained filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washthe solution was washed twice with 6N hydrochloric acid and once with water
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5ee08637e37442cc9068fbfcd5a6adef
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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