N,N-diethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine → 4-(1-(Diethylamino)-2-methylpropan-2-yl)aniline
Reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][C:5]([CH3:16])([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:6])[CH3:2]>[Pd].C(OCC)(=O)C>[CH2:17]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)([CH3:6])[CH3:16])[CH3:18]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 100 mL round bottomed flask was charged N,N-diethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine (1.45 g, 5.79 mmol), ethyl acetate (29 mL) and a nitrogen atmosphere was introduced to the flask. 10% Palladium on activated carbon was carefully introduced and the flask contents were purged (evacuate—backfill) twice with nitrogen and lastly with hydrogen dispensed from a balloon. The reaction was stirred for 16 h under the hydrogen atmosphere. The hydrogen was removed and the solution was filtered over Celite®, rinsed with methanol and the filtrate was concentrated in vacuo to give 4-(1-(diethylamino)-2-methylpropan-2-yl)aniline (1.19 g, 93.5%) as a light yellow oil. LC/MS (ESI+) 221 (M+H)+.