dimethyl[benzyl(methyl)amino]propanedioate → HCID 71268170, compound

HRID 1519653Notes

Reaction equation

HRID 1519653 reaction equation
[CH2:1]([N:8]([CH:10]([C:15]([O:17]C)=O)[C:11]([O:13][CH3:14])=[O:12])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][NH2:20].CO>CO>[CH3:14][O:13][C:11](=[O:12])[CH:10]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:9])[C:15]([NH:20][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 222087dimethyl[benzyl(methyl)amino]propanedioate2×HCID 57454252Monomethylamine methanol

Product 1

HCID 71268170HCID 71268170, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (39 mL) solution of dimethyl [benzyl(methyl)amino]propanedioate (Intermediate 1-2, 13 g), a 9 mol/L-methylamine-methanol solution (14 mL) was added at room temperature, followed by stirring the mixture for 26 hours at room temperature. The reaction mixture was concentrated under reduced pressure, whereafter ethyl acetate and water were added to the resulting residue to isolate the organic layer. The extract was washed with brine, and dried over anhydrous sodium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (hexane/ethyl acetate=50/50→chloroform/acetone=95/5) to obtain ({[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)amino}methyl)benzene (pale yellow oil) (7.1 g, 56%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, whereafter ethyl acetate and water
  2. additionwere added to the resulting residue
  3. customto isolate the organic layer
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThen, the desiccant was filtered out
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by OH type silica gel column chromatography (hexane/ethyl acetate=50/50→chloroform/acetone=95/5)

Sources & evidence

ORD record
ord-47b0a1dca315427aae0647f7124f90eb
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

Loading…