Water → 4-Biphenyl-3-yl-N-pyridin-3-ylpiperazine-1-carboxamide

HRID 1158703Notes

Reaction equation

HRID 1158703 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[C:16]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:21]=[CH:20][CH:19]=[C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:17]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:16]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:21]=[CH:20][CH:19]=[C:18]([N:22]2[CH2:23][CH2:24][N:25]([C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:15])[CH2:26][CH2:27]2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27567121-Biphenyl-3-yl-piperazineHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamate

Product 1

HCID 161138264-Biphenyl-3-yl-N-pyridin-3-ylpiperazine-1-carboxamideYield 58.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (249 mg, 0.923 mmol), 1-biphenyl-3-ylpiperazine (200 mg, 0.839 mmol) and diisopropylethylamine (0.292 ml, 1.68 mmol) in dimethylsulfoxide (2.5 ml) was stirred at 70° C. for 12 hours. To the reaction solution was added water, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduce pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and then recrystallized from a mixed solvent of hexane and ethyl acetate to give the titled compound (176 mg, 58.6%) as solid product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-cc1a9d0dbe4844a28381990d54baac16
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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