Water → N-(3,4-Dimethylisoxazol-5-yl)-4-[3-(3-thienyl)phenyl]piperazine-1-carboxamide

HRID 1158720

Reaction equation

HRID 1158720 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].[S:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:25]=[CH:26][CH:27]=2)=[CH:18]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH3:12][C:9]1[C:8]([CH3:13])=[C:7]([NH:6][C:5]([N:31]2[CH2:32][CH2:33][N:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:19]4[CH:20]=[CH:21][S:17][CH:18]=4)[CH:23]=3)[CH2:29][CH2:30]2)=[O:14])[O:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 589851401-[3-(3-Thienyl)phenyl]piperazineHCID 86245257HCID 86245257, compound

Product 1

HCID 16113933N-(3,4-Dimethylisoxazol-5-yl)-4-[3-(3-thienyl)phenyl]piperazine-1-carboxamideYield 19.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate (129 mg, 0.450 mmol), 1-[3-(3-thienyl)phenyl]piperazine (100 mg, 0.409 mmol) and diisopropylethylamine (0.143 ml, 0.818 mmol) in dimethylsulfoxide (1.5 ml) was stirred at 70° C. for 15 hours. Water was poured into the reaction solution, 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 (hexane:ethyl acetate=3:7), and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the titled compound 30.7 mg (19.6%) 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 (hexane:ethyl acetate=3:7)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-88c75a60a9314b91b8af8dc7309bc0e7
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Linked notes

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