Trifluoroacetic acid → 3-(2-Aminoethyl)benzonitrile

HRID 2239585Notes

Reaction equation

HRID 2239585 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C)[CH:6]=[CH:7][CH:8]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:11][CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86617889Tert-butyl [2-(3-cyanophenyl)ethyl]carbamate

Product 1

HCID 118159283-(2-Aminoethyl)benzonitrileYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl [2-(3-cyanophenyl)ethyl]carbamate (0.949 g, 3.853 mmol) was dissolved in DCM (5 mL) and TFA (4 mL) and stirred at rt for 2 h. The mixture was concentrated and redissolved in EtOAc. The mixture was washed with saturated aqueous K2CO3, dried over Na2SO4, filtered and evaporated affording the title compound (0.40 g, 71.7%). 1H NMR (500 MHz, CDCl3): δ 1.18 (bs, 2H), 2.79 (t, 2H), 3.00 (t, 2H), 7.39-7.47 (m, 2H), 7.50-7.53 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 39.81, 43.42, 112.74, 119.17, 129.47, 130.24, 132.57, 133.66, 141.67.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in EtOAc
  3. washThe mixture was washed with saturated aqueous K2CO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-bca7ac4cc7284bf0bcc89c1bfa41f632
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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