Water → 4-Biphenyl-3-yl-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide

HRID 1158704Notes

Reaction equation

HRID 1158704 reaction equation
ClC(Cl)(Cl)CO[C:5](=[O:14])[NH:6][C:7]1[O:11][N:10]=[C:9]([CH3:12])[C:8]=1[CH3:13].[C:17]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:18]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:17]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:24][CH2:25][N:26]([C:5]([NH:6][C:7]3[O:11][N:10]=[C:9]([CH3:12])[C:8]=3[CH3:13])=[O:14])[CH2:27][CH2:28]2)[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27567121-Biphenyl-3-yl-piperazineHCID 862452572,2,2-Trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate

Product 1

HCID 159507444-Biphenyl-3-yl-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamideYield 62.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate (265 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 14 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:hexane=1:1), and then recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the titled compound (198 mg, 62.6%) 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:hexane=1:1)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-bcaa11f496414869bb89a6e361dc56f4
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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