2,2,2-Trifluoroacetophenone → 1-Phenethylamine

HRID 1585837Notes

Reaction equation

HRID 1585837 reaction equation
FC(C(C1C=CC=CC=1)=O)(F)F.[C:13]1([C@@H:19]([NH2:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1>[C:13]1([CH:19]([NH2:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 99052,2,2-TrifluoroacetophenoneHCID 758181-Phenethylamine, (-)-

Product 1

HCID 74081-PhenethylamineYield 82%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  1. temperaturethe system was refluxed
  2. customThe solvent was removed with the aid of an evaporator

Sources & evidence

ORD record
ord-0e932b9a1c3c49d290cbda29ef34a94e
Source dataset
uspto-grants-1999_08
Patent number
US05939588

Reaction notes

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