1-Amino-2-propanol → HCID 54355367, compound

HRID 2198887Notes

Reaction equation

HRID 2198887 reaction equation
[CH2:1]([C:3]1([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[CH2:5][O:4]1)[CH3:2].[NH2:14][CH2:15][CH:16]([OH:18])[CH3:17]>C(O)C>[CH2:1]([C:3]([CH2:5][NH:14][CH2:15][CH:16]([OH:18])[CH3:17])([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)[OH:4])[CH3:2]

Participants

4

Reactant 2

HCID 41-Amino-2-propanolHCID 20517520HCID 20517520, compound

Product 1

HCID 54355367HCID 54355367, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Ethyl-2-(3-methoxyphenyl)oxiran (14 g, 0.079 mole) and 1-amino-2-propanol (100 g., 1.33 mole) wee refluxed with ethanol (50 ml) for 12 hours. The solvent and excess aminopropanol was removed under reduced pressure. The residue was dissolved in methanol (80 ml) and acidified with ethereal hydrogen chloride. The methanol was evaporated and the residue taken up in water (250 ml). Non-basic material was extracted by shaking the aqueous solution with three portions of 100 ml of ether. The aqueous layer was neutralised with a large excess of 0.880 ammonia, and reextracted with ether (3×100 ml). The ether layers were washed with water and dried (MgSO4). Removal of solvent left the title compound in 98% purity (12.3 g).

Workup

  1. customThe solvent and excess aminopropanol was removed under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (80 ml)
  3. customThe methanol was evaporated
  4. extractionNon-basic material was extracted
  5. washThe ether layers were washed with water
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvent
  8. waitleft the title compound in 98% purity (12.3 g)

Sources & evidence

ORD record
ord-43b066353f7c40b3af4867dd7960388b
Source dataset
uspto-grants-1982_11
Patent number
US04360519

Reaction notes

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