N-Ethyl-N-[(oxiran-2-yl)methyl]aniline → HCID 21312729, compound

HRID 2361866Notes

Reaction equation

HRID 2361866 reaction equation
[CH2:1]([N:3]([CH2:10][CH:11]1C[O:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[CH3:14][O-:15].[Na+].[C:17]([O-])(O)=O.[Na+]>CO>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:10][CH:11]([OH:12])[CH2:14][O:15][CH3:17])[CH3:2]

Participants

5

Reactant 3

HCID 89192N-Ethyl-N-[(oxiran-2-yl)methyl]anilineHCID 516892Sodium BicarbonateHCID 10942334Sodium Methoxide

Product 1

HCID 21312729HCID 21312729, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl-oxiranylmethyl-phenyl-amine (1.72 g, 9.65 mmol) and NaOMe (1.04 g, 2.0 eq.) in MeOH (8 mL) was heated at reflux for over weekend. After cooling to room temperature, the mixture was diluted with sat. NaHCO3 (20 mL) and extracted with 3×20 mL of EtOAc. The combined extracts were dried over Na2SO4, filtered and concentrated and the product was purified by chromatography (30% EtOAc-hexanes) to give 1-(ethyl-phenyl-amino)-3-methoxy-propan-2-ol (1.95 g, 97%).

Workup

  1. temperatureat reflux for over weekend
  2. extractionextracted with 3×20 mL of EtOAc
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe product was purified by chromatography (30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-19121276137f48bdac06026d75bffe0d
Source dataset
uspto-grants-2014_04
Patent number
US08691814B2

Reaction notes

Loading…