Ethanol → 3-Methylamino-1-phenylpropanol

HRID 962940Notes

Reaction equation

HRID 962940 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:3]1.C(O)C>C1S(=O)(=O)CCC1.[Pd]>[CH3:1][NH:2][CH2:6][CH2:5][CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:3]

Participants

5

Reactant 2

HCID 702EthanolHCID 110519812-Methyl-5-phenylisoxazolidine

Product 1

HCID 27339893-Methylamino-1-phenylpropanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31347SulfolaneSolvent

Conditions

Temperature
50 °C

Procedure

2-Methyl-5-phenylisoxazolidine (38.1 g, 234 mmol) dissolved in tetramethylene sulfone (38.1 g) is mixed with 5% Pd/C (1.9 g) in a glass pressure reactor. The reactor is warmed to 50° C. and the pressure is maintained at 40 psig with H2 for 24 hours. Ethanol (38.1 g) is added and heating is continued for 48 hours. After cooling, the mixture is filtered and the EtOH is removed to give a solution of N-methyl-3-phenyl-3-hydroxypropylamine in tetramethylene sulfone.

Workup

  1. temperaturethe pressure is maintained at 40 psig with H2 for 24 hours
  2. temperatureheating
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered
  5. customthe EtOH is removed

Sources & evidence

ORD record
ord-bd5b5c7f1e2c4c538d0515930045b70f
Source dataset
uspto-grants-1998_06
Patent number
US05760243

Reaction notes

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