Potassium Carbonate → [5-Nitro-2-(4-ethylpiperazin-1-yl)phenyl]methanol

HRID 1172615Notes

Reaction equation

HRID 1172615 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O.F[C:15]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:16]=1[CH2:17][OH:18].[CH2:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[CH3:27]>O>[N+:23]([C:20]1[CH:21]=[CH:22][C:15]([N:31]2[CH2:32][CH2:33][N:28]([CH2:26][CH3:27])[CH2:29][CH2:30]2)=[C:16]([CH2:17][OH:18])[CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 791961-EthylpiperazineHCID 4437169(2-Fluoro-5-nitrophenyl)methanol

Product 1

HCID 28963619[5-Nitro-2-(4-ethylpiperazin-1-yl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

4.24 g of potassium carbonate was added to N-methylpyrrolidone (4.24 mL) solution of 4.24 g of 2-fluoro-5-nitrobenzyl alcohol and 4.24 g of N-ethylpiperazine, and stirred at 140° C. for 14 hours. Water was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water in that order, then dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the entitled compound as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated saline water in that order
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2150c44cee1b40cd855583cfcb1b8195
Source dataset
uspto-grants-2010_11
Patent number
US07834019B2

Reaction notes

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