[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.CO.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][CH3:20])[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[NH2:9]A mixture of 1-[3-(methyloxy)-4-nitrophenyl]-4-propylpiperazine (0.204 g, 0.73 mmol) and nickel(II) chloride hexahydrate (0.087 g, 0.37 mmol) was stirred in 2:1 MeOH/THF (7 mL) under N2 at rt. To this mixture was added NaBH4 (0.097 g, 2.6 mmol) in 2 equal portions over 5 min. The reaction was stirred at rt for about 45 min, then concentrated under vacuum. The residue was dissolved in DCM and poured through Celite, washing with DCM and EtOAc. The filtrate was concentrated and chromatographed on silica gel to give the title compound of step B (170 mg, 0.68 mmol, 93%) as a grey oil. 1H NMR (400 MHz, DMSO-d6): δ 6.50 (d, 1H, J=8.25), 6.47 (d, 1H, J=2.38 Hz), 6.26 (dd, 1H, J=2.47 and 8.34 Hz), 4.19 (br s, 2H), 3.72 (s, 3H), 2.90-2.94 (m, 4H), 2.43-2.47 (m, 4H), 2.25 (t, 2H, J=7.42 Hz), 1.44 (q, 2H, J=7.39 Hz), 0.86 (t, 3H, J=7.33 Hz).
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