N-methyl-N-{3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide → N-{3-Amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}-N-methylacetamide

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Reaction Steps

N-Methyl-N-{3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide (21.7 g, 70.5 mmol) was hydrogenated in ethyl acetate (500 mL) catalyzed by 10% Pd/C (1.0 g) at 30-40 psi H2 in Parr shaker for 18 h at room temperature. After filtration through celite and concentration, 19.6 g (100%) of a purple solid was obtained. 1H NMR (400 MHz, CHLOROFORM-D): δ 1.35-1.50 (m, 2 H), 1.67 (s, 1 H), 1.73-1.81 (m, 2 H), 1.88 (s, 3 H), 1.88-1.99 (m, 1 H), 3.04 (d, J=6.64 Hz, 2 H), 3.20 (s, 3 H), 3.33-3.48 (m, 4 H), 3.97-4.08 (m, 2 H), 6.54 (d, J=1.76 Hz, 1 H), 6.60-6.63 (m, 2 H); MS (ESI) (M+H)+: 278.7

Provenance & Evidence