1-Methyl-4-(methylamino)piperidine → 3-[4-(4-Nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea

Participants

Reaction Steps

[4-(4-Nitrophenoxy)pyridin-2-yl]carbamic acid phenyl ester (150 mg) was dissolved in N,N-dimethylformamide (4 ml) under a nitrogen atmosphere, and then N-methyl-N-(1-methylpiperidin-4-yl)amine (0.186 mg) was added thereto, followed by stirring for 1 hr. The reaction mixture was partitioned between ethyl acetate (40 ml) and a saturated aqueous solution of ammonium chloride (10 ml). The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:1, then ethyl acetate). Fractions containing the target compound were concentrated under a reduced pressure to provide 3-[4-(4-nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea (117.7 mg, 71.5%) as a crude product.

Provenance & Evidence