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

HRID 252024Notes

Reaction equation

HRID 252024 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 nmol) 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-3e188c66909e43d2a71348b60b73e6ce
Source dataset
uspto-grants-2011_01
Patent number
US07868002B2

Reaction notes

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