Hydrochloric Acid → HCID 18332940, compound

HRID 2269757Notes

Reaction equation

HRID 2269757 reaction equation
Cl.C([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH:19]=[O:20])[CH:11]([CH2:21][N:22]([CH3:24])[CH3:23])[CH2:10]1)C1C=CC=CC=1>[Pd].CO>[CH3:24][N:22]([CH2:21][CH:11]1[CH2:10][NH:9][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[CH:19]=[O:20])[CH3:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18332990HCID 18332990, compound

Product 1

HCID 18332940HCID 18332940, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd-C (175 mg) and concentrated hydrochloric acid (0.3 ml) were added to a methanol (15 ml) solution of 4-benzyl-2-(N,N-dimethylamino)methyl-1-formyl-1,2,3,4-tetrahydroquinoxaline (350 mg). The reaction mixture was subjected to catalytic hydrogenation at room temperature under 4.5 atmospheric pressure for 2 hours. The catalyst was removed by filtration and the filtrate was concentrated. 10% Aqueous potassium carbonate solution was added to the residue, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated to give 2-(N,N-dimethylamino)methyl-1-formyl-1,2,3,4-tetrahydroquinoxaline (190 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. addition10% Aqueous potassium carbonate solution was added to the residue, which
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d2ce516df8c47eea8ba384b06e457ea
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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