4-(cis-3,5-Dimethyl-1-piperazinyl)-2-nitrobenzonitrile → 2-Amino-4-(cis-3,5-dimethyl-1-piperazinyl)benzonitrile

Reaction equation

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

Participants

Procedure

A solution of the product of Step 1 (186 mg, 0.71 mmol) in ethanol (14 ml) and methanol (3-4 ml) was treated with palladium on charcoal (37 mg, 10% paste) and stirred under an atmosphere of hydrogen for 16 hours. The mixture was then filtered through celite, washing with ethanol and the then evaporated in vacuo. Purification of the residue by mass directed autoprep HPLC gave the title compound (D20) as the formic acid salt. MS (ES+) m/e 231 [M+H]+.