1-Methyl-4-(methylamino)piperidine → Methyl-(1-methyl-piperidin-4-yl)-(5-nitro-benzooxazol-2-yl)-amine

Participants

Reaction Conditions

Reaction Steps

Dissolve 2-ethylsulfanyl-5-nitro-benzooxazole (1.17 g, 5.23 mmol) in anhydrous THF (10 mL) in a reaction tube and blow nitrogen into the vessel for 10 s. Add methyl-(1-methyl-piperidin-4-yl)-amine (1.37 mL, 9.42 mmol) to the solution. Quickly seal the vessel and immerse into a pre-heated oil bath (100° C.) and stir for 24 h. Concentrate the reaction mixture in vacuo, wash with 1.0M NaOH (aq) (2×50 mL), dry over Na2SO4, filter, and concentrate in vacuo. Subject the residue by silica gel flash column chromatography, eluting with 2N NH3 in MeOH/CH2Cl2, to yield the desired product (0.608 g, 40%). MS (ES+) 291.0 (M+1)+.

Provenance & Evidence