Potassium Carbonate → HCID 67106782, compound

HRID 1910798Notes

Reaction equation

HRID 1910798 reaction equation
Cl.[CH3:2][C:3]([NH2:14])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)[CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25]>CN(C=O)C.O>[CH3:25][CH:24]([CH3:26])[C:23](=[O:27])[CH2:22][NH:14][C:3]([CH3:2])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)[CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 108990371-Bromo-3-methylbutan-2-oneHCID 67106609HCID 67106609, compound

Product 1

HCID 67106782HCID 67106782, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-1-(3-nitro-phenyl)-ethylamine hydrochloride (600 mg, 2.8 mmol) in DMF (8 mL) was added anhydrous potassium carbonate (1.5 g, 11 mmol) and 1-bromo-3-methyl-2-butanone (prepared according to Organic Syntheses, Collective Volume 6, page 193) (0.45 mL, 3.62 mmol). The mixture was stirred for 3 h then diluted with water and extracted twice with ethyl acetate. The combined organic phases were washed with water and brine, dried and concentrated to dryness under reduced pressure to afford 3-methyl-1-[1-methyl-1-(3-nitro-phenyl)-ethylamino]-butan-2-one (650 mg, 89%) as an oil which was used immediately in the following step.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic phases were washed with water and brine
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6f39f9d789434fa48630290fd2210478
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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