Ethyl Acetate → 4-(1,4'-Bipiperidin-1'-yl)-2,5-bis(methyloxy)aniline

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[N:14]1[CH2:19][CH2:18][CH:17]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:16][CH2:15]1.CCOC(C)=O>CCO.[Pt]>[N:20]1([CH:17]2[CH2:16][CH2:15][N:14]([C:4]3[C:3]([O:2][CH3:1])=[CH:8][C:7]([NH2:9])=[C:6]([O:12][CH3:13])[CH:5]=3)[CH2:19][CH2:18]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

Procedure

1′-[2,5-Bis(methyloxy)-4-nitrophenyl]-1,4′-bipiperidine (3.0 g, 8.6 mmol) was taken up in EtOH (50 mL) and EtOAc was added to help with solubility. The catalyst, 5% sulfided platinum on carbon (300 mg) was added. The reaction was placed on a Fischer-Porter Hydrogenator under 50 psi of H2 gas and was allowed to stir at rt overnight. The catalyst was filtered off and the filtrate was concentrated in vacuo to give the title compound of step B without further purification (2.72 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.42 (s, 1H), 6.28 (s, 1H), 4.31 (s, 2H), 3.63 (s, 3H), 3.61 (s, 3H), 3.15 (d, J=11.4 Hz, 2H), 2.38-2.47 (m, 6H), 2.20 (t, J=11.5 Hz, 1H), 1.67 (d, J=11.7 Hz, 2H), 1.41-1.53 (m, 6H), 1.34 (d, J=4.8 Hz, 2H).