3-Phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propanenitrile → 3-Phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propan-1-amine
Reaction equation
[C:1]1([CH2:7][C:8]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)[C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO.[Ni]>[C:1]1([CH2:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:19])([F:20])[F:21])[CH:12]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=2)[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)-propanenitrile (2.20 g, 4.88 mmol), prepared as described in Procedure 15, in EtOH (45 mL) was added an aqueous slurry of Raney 2800 nickel (4 mL). The reaction mixture was stirred under an atmosphere of hydrogen (70 psi) for 42 h. The reaction mixture was filtered through celite and concentrated under reduced pressure to give 3-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propan-1-amine (2.04 g, 92% yield) as a clear, colorless oil. LCMS: RT=1.87 min [M+H] 456.2 (2 min Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm); NMR: 400 MHz 1H (CDCl3) ppm 3.21 (s, 2 H), 3.45 (s, 2 H), 6.59 (d, J=7.03 Hz, 2 H), 6.92 (s, 2 H), 7.01-7.15 (m, 7 H), 7.31 (t, J=8.13 Hz, 2 H).
Workup
- filtrationThe reaction mixture was filtered through celite and
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-022262ed646f426c9513e1f4dabe2af7
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102599B2
Reaction notes
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