Water → Ethyl-methyl-{3-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-prop-2-ynyl}-amine

Participants

Reaction Steps

To a stirred solution of 3-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-prop-2-yn-1-ol (as prepared in the previous step, 47 mg, 0.17 mmol) in 4 mL of DCM at 0° C. was added triethylamine (71 μL, 0.51 mmol) followed by methanesulfonyl chloride (17 μL, 0.22 mmol). The reaction was allowed to stir for 10 min, at which time ethylmethylamine (4 drops) was added. The result was heated at reflux for 20 min. and then poured into water (20 mL). The aqueous layer was extracted with DCM (2×25 mL), the organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by preparative TLC (10%-MeOH—CHCl3) to afford 59 mg (100%) of the title compound as an oil. Mass spectrum (ESI, m/z) Calcd for C18H25N3O2, 316.1 (M+H). found 316.2.

Provenance & Evidence