Piperazine → HCID 67042029, compound

HRID 716878Notes

Reaction equation

HRID 716878 reaction equation
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CS(C)=O>[C:16]1([C:3]2[C:2]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 67042029HCID 67042029, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

A solution of methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (150 mg, 0.44 mmol, 1.00 equiv) and piperazine (77.4 mg, 0.90 mmol, 2.00 equiv) in DMSO (8 mL) was placed in a 20-mL sealed tube, stirred for 3 hrs at 125° C. in an oil bath, and then quenched by the addition of 50 mL of water. The resulting solution was extracted with 6×50 mL of dichloromethane, the organic layers combined and dried over anhydrous sodium sulfate, and the solution filtered to remove solids. Concentration under vacuum yielded 160 mg (91%) of methyl 2-phenyl-3-(piperazin-1-yl)quinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customsealed tube
  2. customquenched by the addition of 50 mL of water
  3. extractionThe resulting solution was extracted with 6×50 mL of dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationthe solution filtered
  6. customto remove solids
  7. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-6c2bfaf8c7dc475bbceb2526060b112d
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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