1,2-Dibromoethane → HCID 86713221, compound

HRID 1056822Notes

Reaction equation

HRID 1056822 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[H-].[Na+].[CH2:14](Br)[CH2:15]Br.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CN(C)C=O.O>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([O:1][CH2:24][CH2:23][N:22]2[CH2:15][CH2:14][N:19]([CH3:18])[CH2:20][CH2:21]2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 531671-MethylpiperazineHCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 86713221HCID 86713221, compoundYield 20.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 304 mg (2.00 mmol) of 4-hydroxy-2-methoxybenzaldehyde in N,N-dimethylformamide (4.0 mL) was added 105 mg (55%, 2.40 mmol) of sodium hydride at room temperature. The mixture was stirred at room temperature for 30 minutes, and 0.69 mL (8.0 mmol) of ethylene dibromide was added thereto. The mixture was stirred at 80° C. for 7 hours, and 2.2 mL (20 mmol) of 1-methylpiperazine was added thereto. The mixture was stirred at 80° C. overnight. Water was added to the reaction mixture under ice-cooling and extraction with ethyl acetate was performed. The resulting organic layer was washed with saturated sodium bicarbonate solution and then with saturated brine and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0 to 40/60) to give 115 mg (20% yield) of the title compound as a brown viscous matter.

Workup

  1. stirringThe mixture was stirred at 80° C. for 7 hours
  2. stirringThe mixture was stirred at 80° C. overnight
  3. temperaturecooling
  4. extractionextraction with ethyl acetate
  5. washThe resulting organic layer was washed with saturated sodium bicarbonate solution
  6. dry with materialwith saturated brine and dried over magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0 to 40/60)

Sources & evidence

ORD record
ord-5cfa6e3a81b24ddc807a4c23cd9be065
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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