Hydrazine → (R)-(+)-beta-Methylphenethylamine

HRID 2085451Notes

Reaction equation

HRID 2085451 reaction equation
[C:1]1([C@@H:7]([CH3:20])[CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN>C1(C)C=CC=CC=1>[C:1]1([C@@H:7]([CH3:20])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 213073412-((2R)-2-phenylpropyl)isoindoline-1,3-dione

Product 1

HCID 1547949(R)-(+)-beta-MethylphenethylamineYield 94.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 500 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer and addition funnel is charged with 2-((2R)-2-phenylpropyl)isoindoline-1,3-dione (11.54 g, 43.49 mmol), toluene (200.0 mL) and anhydrous hydrazine (2.73 mL, 86.99 mmol). Reaction is then stirred at room temperature for 3.0 hours and then heated at 90° C.-95° C. for 2.0 hours. Cooled the slurry to room temperature, filtered precipitates, then concentrated filtrate to provide the intermediate title compound, (2R)-2-phenylpropylamine, (5.58 g, 94.9%) an oil; 1H nmr (CDCl3, 300 MHz) δ 1.21 (d, 3H), 1.40-1.60 (b, 2H), 2.68-2.80 (m, 1H), 2.81-2.87 (m, 2H) 7.20 (m, 2H), 7.32 (m, 2H).

Workup

  1. additionthermometer and addition funnel
  2. customReaction
  3. temperatureheated at 90° C.-95° C. for 2.0 hours
  4. temperatureCooled the slurry to room temperature
  5. filtrationfiltered
  6. customprecipitates

Sources & evidence

ORD record
ord-2f15f632474c4f69b1ebb70c6052572f
Source dataset
uspto-grants-2004_04
Patent number
US06720357B2

Reaction notes

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