Hydrochloric Acid → HCID 15870800, compound

Participants

Reaction Steps

To a 200 mL round bottomed flask with a stirring bar and a gas dispersion tube was added N-(2-methyl-4-(2-(N,N-dimethylamino)ethoxy)phenyl)-4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)benzamide (0.295 g, 0.61 mmol) and 50 mL of dry EtOAc. This well stirred solution was cooled in an ice bath and saturated with HCl gas over 15 min. The mixture was aged 1 h at 0° C. and the excess HCl was then removed with a stream of argon. The EtOAc was removed in vacuo and the crude product was partitioned between EtOAc and NaHCO3 solution. The layers were separated, the organic phase was washed with brine and dried (MgSO4). Filtration, removal of the solvent in vacuo and recrystallization from EtOAc gave 0.145 g of N-(2-methyl-4-(2-(N,N-dimethyl)aminoethoxy)phenyl)-4-(1-piperazinyl)benzamide, as a white crystals. mp: 139-141° C. 1H NMR (CDCl3): d 1.66 (br s, 1H), 2.28 (s, 3H), 2.33 (s, 6H), 2.72 (t, j=6 Hz, 2H), 3.05 (m, 4H), 3.27 (m, 4H), 4.05 (t, j=6 Hz, 2H), 6.77 (m, 2H), 6.93 (d, j=9 Hz, 2H), 7.45 (s, 1H), 7.63 (d, j=9 Hz, 1H), 7.77 (d, j=9 Hz, 2H).

Provenance & Evidence