Sodium Hydroxide → 3-Methylamino-1-phenylpropanol

HRID 1417059Notes

Reaction equation

HRID 1417059 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 (K2CO)3 and concentrated to give N-methyl-3-phenyl-3-hydroxypropylamine.

Workup

  1. temperatureheating
  2. extractionextracted with chloroform
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-877a731ee09d46c1958e05c62a5748e2
Source dataset
uspto-grants-1999_06
Patent number
US05917091

Reaction notes

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