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

HRID 1630362Notes

Reaction equation

HRID 1630362 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-0a63a868e52d475cbec4e5efdd90495c
Source dataset
uspto-grants-2014_07
Patent number
US08791125B2

Reaction notes

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