2-[(3,5-Bis-trifluoromethyl-benzyl)-ethyl-amino]-5-trifluoromethyl-benzaldehyde oxime → (2-Aminomethyl-4-trifluoromethyl-phenyl)-(3,5-bis-trifluoromethyl-benzyl)-ethyl-amine
Reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][N:7]([CH2:21][CH3:22])[C:8]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:9]=1[CH:10]=[N:11]O>CO.[Ni]>[NH2:11][CH2:10][C:9]1[CH:13]=[C:14]([C:17]([F:19])([F:20])[F:18])[CH:15]=[CH:16][C:8]=1[N:7]([CH2:6][C:5]1[CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:4]=1)[CH2:21][CH3:22]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2-[(3,5-Bis-trifluoromethyl-benzyl)-ethyl-amino]-5-trifluoromethyl-benzaldehyde oxime (241 mg) is dissolved in methanol (10 ml) and thereto is added Raney nickel (0.5 g) and the mixture is stirred under hydrogen atmosphere at room temperature overnight. Raney nickel is removed by filtration and the filtrate is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→0:1) to give (2-aminomethyl-4-trifluoromethyl-phenyl)-(3,5-bis-trifluoromethyl-benzyl)-ethyl-amine (210 mg). MS (m/z): 445 [M+H]+
Workup
- customRaney nickel is removed by filtration
- concentrationthe filtrate is concentrated under reduced pressure
- customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→0:1)
Sources & evidence
- ORD record
- ord-3948905d06ac45ac9789e55d354e1e16
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906517B2
Reaction notes
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