Sodium Methoxide → 1-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxyquinoxalin-2(1H)-one

HRID 656993Notes

Reaction equation

HRID 656993 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19](F)[CH:20]=3)[N:15]=[CH:14][C:13]2=[O:23])[CH2:6][CH2:5]1.[CH3:24][O-:25].[Na+]>CO.[Cl-].[NH4+]>[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:25][CH3:24])[CH:20]=3)[N:15]=[CH:14][C:13]2=[O:23])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 688175421-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride

Product 1

HCID 593978381-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxyquinoxalin-2(1H)-oneYield 66%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride (0.363 g, 1 mmol) in dry MeOH (5 ml) was added a 25 wt. % solution of sodium methoxide in MeOH (0.87 ml, 4 mmol). After heating under reflux overnight, a further portion of sodium methoxide solution (0.22 ml) was added and heating was continued for 24 h. Aqueous ammonium chloride 96 drops) was added and the mixture was evaporated to dryness. The residue was extracted several times with 10% MeOH/DCM, and the extracts were filtered and evaporated. The residue was chromatographed on silica, eluting with 0-20% (2M ammonia/MeOH)/DCM to give the product (0.20 g, 66%).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux overnight
  3. temperatureheating
  4. customthe mixture was evaporated to dryness
  5. extractionThe residue was extracted several times with 10% MeOH/DCM
  6. filtrationthe extracts were filtered
  7. customevaporated
  8. customThe residue was chromatographed on silica
  9. washeluting with 0-20% (2M ammonia/MeOH)/DCM

Sources & evidence

ORD record
ord-f35a6a8f6c634e93a665736f3d36a931
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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