1-Phenylpiperazine → HCID 67167457, compound

HRID 1405259Notes

Reaction equation

HRID 1405259 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[F:22][C:23]1[CH:24]=[C:25]([N+:30]([O-:32])=[O:31])[CH:26]=[CH:27][C:28]=1F>C(OCC)(=O)C>[F:22][C:23]1[CH:24]=[C:25]([N+:30]([O-:32])=[O:31])[CH:26]=[CH:27][C:28]=1[N:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 67167457HCID 67167457, compoundYield 96.33%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

50 ml of ethyl acetate, 13.5 ml of 4-phenyl piperazine, and 15.30 ml of diisopropyl ethyl amine were added into a 250 ml triple-neck flask. After magnetic stirring at room temperature, 9.0 ml of 3,4-difluoro-nitrobenzene was added. The reaction was carried out for 105 hours, followed by extraction with 150 ml of ethyl acetate for three times (150 ml×3). The extract was washed three times with saturated NaCl solution (150 ml×3), dried with anhydrous magnesium sulfate (MgSO4), and evaporated to dryness. An orange yellow solid was obtained which was recrystallized with a mixture of acetone and water in volumetric ratio of 9:1 to produce orange yellow crystals (23.66 g) with a yield of 96.33%.

Workup

  1. extractionfollowed by extraction with 150 ml of ethyl acetate for three times (150 ml×3)
  2. washThe extract was washed three times with saturated NaCl solution (150 ml×3)
  3. dry with materialdried with anhydrous magnesium sulfate (MgSO4)
  4. customevaporated to dryness
  5. customAn orange yellow solid was obtained which
  6. customwas recrystallized with a mixture of acetone and water in volumetric ratio of 9:1

Sources & evidence

ORD record
ord-08522411f986470189ff0a17e5ca754d
Source dataset
uspto-grants-2014_12
Patent number
US08916567B2

Reaction notes

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