Trifluoroacetic acid → 4-(2-Aminoethyl)benzonitrile

HRID 1506149Notes

Reaction equation

HRID 1506149 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH2:8][NH:9]C(=O)OC(C)(C)C)=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[NH2:9][CH2:8][CH2:7][C:6]1[CH:17]=[CH:18][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21955533tert-Butyl 4-cyanophenethylcarbamate

Product 1

HCID 219125254-(2-Aminoethyl)benzonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-cyanophenethylcarbamate (305 mg, 1.24 mmol) in dichloromethane (4 mL) was mixed with trifluoroacetic acid (3.50 mL, 47.1 mmol) under cooling with ice and then stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, mixed with saturated aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as a pale orange solid (72.5 mg, yield 40%).

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionmixed with saturated aqueous potassium carbonate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9999292718f04924bdd8c1cdc9c80ea9
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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