Methylamine → 1-Methylamino-3-phenoxy-propan-2-ol

HRID 543666Notes

Reaction equation

HRID 543666 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1.[CH3:12][NH2:13]>C(O)C.O>[CH3:12][NH:13][CH2:2][CH:3]([OH:1])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 31217Phenyl glycidyl ether

Product 1

HCID 31483571-Methylamino-3-phenoxy-propan-2-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1,2-epoxy-3-phenoxypropane (15 g), in ethanol (50 ml) was added 25-30% methylamine in water (50 ml) and the mixture heated under reflux for 1 h. The ethanol was removed in vacuo and the residue acidified with 2 N hydrochloric acid. The aqueous solution was extracted with ethyl acetate then made alkaline with 2 N sodium hydroxide and extracted into ether. The combined ethereal extracts were dried (Na2SO4), filtered and evaporated to give a semi-solid (14.8 g). The product was distilled in vacuo to give the title compound as white crystals b.p. 110°/0.07 mm, m.p. 74°-77° (9 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 h
  3. customThe ethanol was removed in vacuo
  4. extractionThe aqueous solution was extracted with ethyl acetate
  5. extractionextracted into ether
  6. dry with materialThe combined ethereal extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-34f2d98842cb476c9295eb6af4412459
Source dataset
uspto-grants-1984_05
Patent number
US04447428

Reaction notes

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