Sodium Hydroxide → 3-Methylamino-1-phenylpropanol

HRID 610627Notes

Reaction equation

HRID 610627 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-hydroxypropyl-amine.

Workup

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

Sources & evidence

ORD record
ord-2ee4f3a234664413a18b56ae7354b96c
Source dataset
uspto-grants-1999_12
Patent number
US05998627

Reaction notes

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