Dimethyl Sulfoxide → 4-(4-Phenylpyridin-2-yl)-N-pyridin-3-ylpiperazine-1-carboxamide

HRID 1158709Notes

Reaction equation

HRID 1158709 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:22]2[CH:27]=[CH:26][N:25]=[C:24]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:16]1([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([N:28]3[CH2:33][CH2:32][N:31]([C:8]([NH:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:30][CH2:29]3)[CH:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 226401171-(4-Phenylpyridin-2-yl)piperazineHCID 68575380HCID 68575380, compound

Product 1

HCID 161138284-(4-Phenylpyridin-2-yl)-N-pyridin-3-ylpiperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (113 mg, 0.418 mmol), 1-(4-phenylpyridin-2-yl)piperazine (100 mg, 0.418 mmol), diisopropylethylamine (0.146 ml, 0.836 mmol) and dimethylsulfoxide (2 ml) was stirred at 70° C. for 12 hours, then the reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduce pressure, and the residue was purified by basic silica gel column chromatography (ethyl acetate) to give the titled compound as solid product. This was recrystallized from a mixed solvent of hexane and ethyl acetate to give the titled compound 67.2 mg (44.8%) 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 basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-0dbacb319e154550be026529ddbca620
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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