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

HRID 647494Notes

Reaction equation

HRID 647494 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-471382e7191246d88e9172da961b9399
Source dataset
uspto-grants-1983_10
Patent number
US04409213

Reaction notes

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