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

HRID 2286354Notes

Reaction equation

HRID 2286354 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 ether 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 ether acetate
  5. extractionextracted into ether
  6. dry with materialThe combined ethereal extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4a7a4b5041404e9c9e9883b0b4b46057
Source dataset
uspto-grants-1981_05
Patent number
US04265891

Reaction notes

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