Sodium Hydroxide → 3-Methylamino-1-phenylpropanol

HRID 962938Notes

Reaction equation

HRID 962938 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-hydroxypropylamine.

Workup

  1. temperatureheating
  2. extractionextracted with chloroform
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a286e8c2ee0f41f3b7b4351ff84e020d
Source dataset
uspto-grants-1998_06
Patent number
US05760243

Reaction notes

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