Trifluoroacetic acid → 3-(2-Aminoethyl)benzonitrile

HRID 2421988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421988
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 118159283-(2-Aminoethyl)benzonitrileAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-97293c70bc0b4d9c828cdb4bbd2f1047
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960380B2

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