Sodium Hydroxide → 3-Methylamino-1-phenylpropanol

HRID 443168Notes

Reaction equation

HRID 443168 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.[OH-].[Na+]>C(O)(=O)C.[Zn]>[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 14798Sodium HydroxideHCID 110519812-Methyl-5-phenylisoxazolidine

Product 1

HCID 27339893-Methylamino-1-phenylpropanol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

2-Methyl-5-phenylisoxazolidine (2.0 g, 12.3 mmol) and Zn powder (1.2 g, 18.3 mmol) in 10 molar aqueous acetic acid are heated to 65°-70° C. for 4 hours. Additional Zn powder (0.4 g, 6.1 mmol) is added and heating is continued for one more hour. The reaction mixture is neutralized with sodium hydroxide and extracted with chloroform. The extract is dried (K2CO3) and concentrated to give N-methyl-3-phenyl-3-hydroxy-propyl-amine.

Workup

  1. temperatureheating
  2. extractionextracted with chloroform
  3. dry with materialThe extract is dried (K2CO3)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a1e50ad53f4948f090fc780841a4b21f
Source dataset
uspto-grants-1999_04
Patent number
US05892117

Reaction notes

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