Methylamine → 8-(N-Methyl)aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

HRID 1059426Notes

Reaction equation

HRID 1059426 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.[CH3:20][NH2:21]>CO>[CH3:20][NH:21][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1133536310-methoxymethyl-8-chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Product 1

HCID 186703078-(N-Methyl)aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-Chloromethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine was stirred in a solution of methylamine in methanol at room temperature over day and night. Then the reaction mixture was distilled under reduced pressure and the residue was distributed into sodium hydroxide and ethyl acetate. The organic layer was extracted and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give the title compound as a yellow oily substance.

Workup

  1. distillationThen the reaction mixture was distilled under reduced pressure
  2. extractionThe organic layer was extracted
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-1d5af62ee1cb45208655f8c0f8690b15
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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