1-Methylpiperazine → HCID 67041699, compound

HRID 716876Notes

Reaction equation

HRID 716876 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.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CS(C)=O.C(Cl)Cl.O>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:2]2[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 67041699HCID 67041699, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21908982Water methylene chlorideSolvent

Procedure

Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (150 mg, 0.44 mmol, 1.00 equiv) in DMSO (8 mL) and 1-methylpiperazine (90 mg, 0.90 mmol, 2.00 equiv) were stirred for 2 hours at 125° C. in an oil bath in a 20-mL sealed tube. The resulting solution was diluted with 20 ml of DCM/H2O (1:1), extracted with 4×40 mL of DCM, and the organic layers combined. The mixture was dried over Na2SO4, filtered to remove solids, and then concentrated under vacuum, resulting in 200 mg (crude) of methyl 3-(4-methylpiperazin-1-yl)-2-phenylquinoxaline-6-carboxylate as a brown solid.

Workup

  1. customsealed tube
  2. extractionextracted with 4×40 mL of DCM
  3. dry with materialThe mixture was dried over Na2SO4
  4. filtrationfiltered
  5. customto remove solids
  6. concentrationconcentrated under vacuum
  7. customresulting in 200 mg (crude) of methyl 3-(4-methylpiperazin-1-yl)-2-phenylquinoxaline-6-carboxylate as a brown solid

Sources & evidence

ORD record
ord-6f6d4916200e4d35b66d39aa15abd27b
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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