HCID 59442047, compound → HCID 59442050, compound

Participants

Reaction Steps

1-methyl-4-(3-{[3-(methyloxy)-4-nitrophenyl]oxy}propyl)piperazine (1.8 g, 5.8 mmol) was dissolved in methanol (75 mL) and cycled through the H-Cube using a Pd/C cartridge. After 60 min of cycling through the system, the solvent was removed under reduced pressure. NMR indicates starting material still present so residue was dissolved in ethanol and 5% platinum on carbon (200 mg) was added and subjected to a H2 balloon for 16 h. At this time the reaction mixture was filtered through celite which was washed with methanol. The solvents were evaporated under reduced pressure to afford 2-(methyloxy)-4-{[3-(4-methyl-1-piperazinyl)propyl]oxy}aniline (1.1 g, 3.75 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.83 (d, J=5.68 Hz, 2 H) 2.41-2.51 (m, 3 H overlaying with DMSO peak) 2.51-2.99 (m, 10 H) 3.68 (s, 3 H) 3.83 (t, J=6.23 Hz, 2 H) 6.24 (dd, J=8.42, 2.56 Hz, 1 H) 6.39 (d, J=2.47 Hz 1 H) 6.49 (d, J=8.42 Hz, 1 H). ESIMS (M+H)+=311.

Provenance & Evidence