Formaldehyde → HCID 15261642, compound

HRID 499162Notes

Reaction equation

HRID 499162 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[CH2:11]=O>C1COCC1>[C:5]1([CH:3]2[O:4][CH2:11][NH:1][CH2:2]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 1000Phenylethanolamine

Product 1

HCID 15261642HCID 15261642, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-1-phenylethanol (1.000 g, 0.007 mmol) and formaldehyde (37%, 0.92 mL, 0.012 mmol) in THF (10 mL) was heated to reflux for 3 h and allowed to cool to ambient temperature with stirring over night. The mixture was concentrated and the residue was dissolved in dichloromethane. The resulting solution was washed with water. The organic phase was dried over anhydrous sodium sulphate, concentrated in vacuo. The yellowish residue was purified by column chromatography to obtain the title compound in 91% yield (0.990 g). MS (ES+) m/z 419.2 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washThe resulting solution was washed with water
  6. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe yellowish residue was purified by column chromatography

Sources & evidence

ORD record
ord-0aed293917a64a20b0d38d5fcad4c840
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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