N-[1-(3-Pentafluoroethyl-phenyl)-vinyl]-acetamide → 1-(3-Pentafluoroethyl-phenyl)-ethylamine

HRID 1098750Notes

Reaction equation

HRID 1098750 reaction equation
[F:1][C:2]([F:19])([C:7]1[CH:8]=[C:9]([C:13]([NH:15]C(=O)C)=[CH2:14])[CH:10]=[CH:11][CH:12]=1)[C:3]([F:6])([F:5])[F:4]>CO>[F:1][C:2]([F:19])([C:7]1[CH:8]=[C:9]([CH:13]([NH2:15])[CH3:14])[CH:10]=[CH:11][CH:12]=1)[C:3]([F:4])([F:6])[F:5]

Participants

3

Reactant 1

HCID 59506293N-[1-(3-Pentafluoroethyl-phenyl)-vinyl]-acetamide

Product 1

HCID 723100481-(3-Pentafluoroethyl-phenyl)-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[1-(3-Pentafluoroethyl-phenyl)-vinyl]-acetamide (110 mg, 0.39 mmol) in methanol (10 ml) was added (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium (I) trifluoromethanesulfonate (0.3 mg). The reaction mixture was hydrogenated with H2 at 5 bar and evaporated. The residue was dissolved in ethanol and hydrochloric acid (6 M, 0.7 ml) and the solution was refluxed for 2 days. Purification by preparative HPLC and lyophilization of the relevant fractions gave the desired product.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethanol
  3. temperaturehydrochloric acid (6 M, 0.7 ml) and the solution was refluxed for 2 days
  4. customPurification by preparative HPLC and lyophilization of the relevant fractions

Sources & evidence

ORD record
ord-68bd9dcb77a841f693a53736ac5ad86d
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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