Trifluoroacetic acid → 4-(2-Aminoethyl)benzonitrile

HRID 1441686Notes

Reaction equation

HRID 1441686 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C>ClCCl>[NH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 21955533tert-Butyl 4-cyanophenethylcarbamate

Product 1

HCID 219125254-(2-Aminoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.90 g commercially available [2-(4-Cyano-phenyl)-ethyl]-carbamic acid tert-butyl ester were dissolved in 100 ml dichloromethane. 10 ml trifluoroacetic acid were added and the reaction mixture was stirred at room temperature for one hour. 250 ml ethyl acetate were added and the mixture was washed three times with saturated NaHCO3 solution. The organic layer was dried over MgSO4 and then the solvent was removed in vacuo to obtain 700 mg 4-(2-Amino-ethyl)-benzonitrile as pale yellow solid.

Workup

  1. washthe mixture was washed three times with saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1f50f452ad114a5f9558744c8ad85374
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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