Water → HCID 16114035, compound

HRID 1158723Notes

Reaction equation

HRID 1158723 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.[O:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:24]=[CH:25][CH:26]=2)=[CH:17]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[O:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]([N:27]3[CH2:32][CH2:31][N:30]([C:8]([NH:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:29][CH2:28]3)[CH:24]=[CH:25][CH:26]=2)=[CH:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 58985096HCID 58985096, compoundHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamate

Product 1

HCID 16114035HCID 16114035, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (279 mg, 1.04 mmol), 1-[3-(3-furyl)phenyl]piperazine (215 mg, 0.942 mmol) and diisopropylethylamine (0.328 ml, 1.88 mmol) in dimethylsulfoxide (3.0 ml) was stirred at 70° C. for 3 days. 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 (ethyl acetate), and recrystallized from a mixed solvent of hexane and ethyl acetate to give the titled compound 147 mg (44.7%) 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-1f8874be2f4f4af19eaccf3b6af24245
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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