2,2,2-Trifluoroacetophenone → 1-Phenethylamine

Participants

Reaction Steps

Trifluoromethylphenyl ketone (348 mq, 2 mmol) and (S)-1-phenylethylamine (242 mg, 2 mmol) were metered out into a 50-mL round-bottom flask, 20 mL benzene was added, a Dean-Stark trap was mounted, and the system was refluxed. The solvent was removed with the aid of an evaporator, and 1a was produced at a yield of 82%. Rf 0.45 (hex/AcOEt=4:1) 1H NMR d 1.44 (d, 3H, J=6.6 Hz), 4.54 (q,1H, J=6.6 Hz), 7.17-7.35 (m, 8H), 7.47-7.50 (m, 2H); 19F NMR d -71.63(s). 13C NMR d 24.53(s), 61.38(s), 119.77(q, JCF =278.8 Hz), 126.45(s), 127.24(s), 127.60(s), 128.61(s). 128.77(s), 130.02(s), 130.56(s), 143.76(s), 156.58(q, JCF =33.2 Hz). MS 277 (M, 7.6), 262 (M-Me, 2.1), 105(100). Anal. Calcd for C16H14F3N: C, 69.31; H, 5.09; N, 5.05; F, 20.55. Found: C, 69.43; H, 5.19; N, 5.05; F, 20.33.

Provenance & Evidence