N-[(5-Chloro-2-isopropylphenyl)methylene]cyclopropanamine → N-(5-chloro-2-isopropylbenzyl)cyclopropanamine
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]([CH3:15])[CH3:14])=[C:6]([CH:8]=[N:9][CH:10]2[CH2:12][CH2:11]2)[CH:7]=1>[Pt].CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]([CH3:15])[CH3:14])=[C:6]([CH:7]=1)[CH2:8][NH:9][CH:10]1[CH2:12][CH2:11]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Platinum on activated carbon (5 g, 5% Pt, dry) was added to a solution of N-[(5-chloro-2-isopropylphenyl)methylene]cyclopropanamine (III) (160.8 g, 0.725 mol) in methanol (1350 ml). The reaction vessel was subsequently flushed with nitrogen and pressurized with 6 bar of hydrogen at a maximum of 25° C. for 8 hours. The contents of the autoclave were filtered through Celite, washed with methanol and the solvent was distilled off under reduced pressure. N-(5-Chloro-2-isopropylbenzyl)cyclopropanamine of the formula (I) (153.5 g, 97.1 GC-% by area, 91.9% of theory) was obtained as a light-yellow oil.