Dimethyl Sulfoxide → 4-[4-(2-Hydroxyethyl)piperazin-1-yl]-2-nitrobenzaldehyde

HRID 1821406Notes

Reaction equation

HRID 1821406 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.O[CH:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:15].CS(C)=[O:24]>O>[OH:24][CH2:15][CH2:14][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 762264-Fluoro-2-nitrobenzaldehydeHCID 177695631-(Piperazin-1-yl)ethan-1-ol

Product 1

HCID 866282154-[4-(2-Hydroxyethyl)piperazin-1-yl]-2-nitrobenzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoro-2-nitrobenzaldehyde (0.20 g, 1.2 mmol), 1-hydroxyethylpiperazin (0.80 mL, 6.5 mmol) and DMSO (3.5 mL) were added and stirred at 100° C. for 1.5 hours. The reaction mixture was added with water and was washed with hexane/ethyl acetate=4/1 to remove impurities. After removing impurities, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure to obtain 4-[4-(2-hydroxyethyl)piperazin-1-yl]-2-nitrobenzaldehyde (0.34 g, 100%).

Workup

  1. washwas washed with hexane/ethyl acetate=4/1
  2. customto remove impurities
  3. customAfter removing impurities
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f5afdda96a264b37b246d0422d2e2cee
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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