[CH3:1][N:2]([CH3:20])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([O:18][CH3:19])[CH:10]=2)[CH2:5][CH2:4]1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([N:6]2[CH2:7][CH2:8][CH:3]([N:2]([CH3:1])[CH3:20])[CH2:4][CH2:5]2)=[CH:10][C:11]=1[O:18][CH3:19]To a solution of nickel (II) chloride hexahydrate (0.58 g, 2.5 mmol) and N,N-dimethyl-1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinamine (1.37 g, 4.90 mmol) in MeOH (25 mL) cooled to 0° C. was added NaBH4 (280 mg, 7.4 mmol) slowly to avoid foaming. When TLC indicated the consumption of starting material, the solution was concentrated to a purple residue. The purple residue was taken up in EtOAc and filtered through a pad of celite. The yellow filtrate was concentrated onto silica gel and purified by flash column chromatography to give the title compound of step B (0.88 g, 74%). 1H NMR (400 MHz, DMSO-d6) δ 6.48-6.45 (m, 2H), 6.26 (dd, J=8.2 and 2.2 Hz, 1H), 4.17 (br s, 2H), 3.70 (s, 3H), 3.38 (d, J=12.4 Hz, 2H), 2.49-2.43 (m under DMSO peak, 2H), 2.16 (s, 6H), 2.11-2.04 (m, 1H), 1.78 (d, J=12.4 Hz, 2H), 1.50-1.40 (m, 2H).
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