Trifluoroacetic acid → 4-(2-Aminoethyl)benzonitrile

HRID 2239559Notes

Reaction equation

HRID 2239559 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][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 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl [2-(4-cyanophenyl)ethyl]carbamate (1.14 g, 4.62 mmol) was dissolved in DCM (6 mL) and TFA (5 mL) was added. The mixture was concentrated and dissolved in EtOAc, and the organic phase was washed with saturated aqueous K2CO3. The organic layer was dried with Na2SO4, filtered and evaporated affording the title compound (0.50 g, 74.3%). 1H NMR (500 MHz, CDCl3): δ 1.21 (bs, 2H), 2.81 (t, 2H), 2.99 (t, 2H), 7.31 (d, 2H), 7.58 (d, 2H); 13C NMR (125 MHz, CDCl3): δ 40.38, 43.31, 110.33, 119.23, 129.86, 132.48, 145.93.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washthe organic phase was washed with saturated aqueous K2CO3
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e482b70022d04d83be2e3b5f09f9f809
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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