4-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine → 4-cyclopropyl-N1-(3-(dimethylamino)propyl)-N1-methylbenzene-1,2-diamine

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[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N:10]([CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH3:11])=[C:6]([N+:18]([O-])=O)[CH:5]=2)[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[CH:1]1([C:4]2[CH:5]=[C:6]([NH2:18])[C:7]([N:10]([CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH3:11])=[CH:8][CH:9]=2)[CH2:2][CH2:3]1

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실험 절차

4-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine (Step 2, 600 mg, 2.16 mmol) was dissolved in 22 mL MeOH. Palladium (115 mg, 0.108 mmol, 10% w/w on carbon) was added, a balloon containing hydrogen was inserted, and the reaction was stirred at RT for 18 h. The solution was then filtered through a pad of Celite and concentrated, yielding the title compound as viscous red-brown oil. MS (M+H+)=248; Calc'd for C15H25N3=247.38.