Sodium Hydroxide → (R)-(+)-beta-Methylphenethylamine

HRID 2085448Notes

Reaction equation

HRID 2085448 reaction equation
C(O)(=O)C(CC(O)=O)O.[C:10]1([C@@H:16]([CH3:19])[CH2:17][NH2:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>C(Cl)Cl>[C:10]1([C@@H:16]([CH3:19])[CH2:17][NH2:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21356831(2R)-2-phenylpropylamine malate

Product 1

HCID 1547949(R)-(+)-beta-Methylphenethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of (2R)-2-phenylpropylamine malate (24.3 g, 0.0601 mol, prepared directly above) in CH2Cl2 (200 mL) was added 1.0 N NaOH dropwise at room temperature. The organic phase was isolated, extracted with brine (1×125 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to give (2R)-2-phenylpropylamine (19 g) as a clear, colorless oil.

Workup

  1. customThe organic phase was isolated
  2. extractionextracted with brine (1×125 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f91eeee381cc4b66ad5c6a4503b88760
Source dataset
uspto-grants-2004_04
Patent number
US06720357B2

Reaction notes

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