4-Methylpiperidine → HCID 10478369, compound

Participants

Reaction Steps

To a solution of N-(3-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide (0.040 g, 0.09 mmol) in 2 mL methylene chloride was added 4-methylpiperidine (0.015 g, 0.15 mmol) and NaB(OAc)3H (0.047 g, 0.22 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (10% methanol/methylene chloride) followed by further medium-pressure chromatography (40% ethyl acetate/hexanes) afforded a mixture comprising 0.008 g of N-(3-hydroxy-benzyl)-2,4,6-trimethyl-N-{4-[3-(4-methyl-piperidin-1-yl)-propyl]-phenyl}-benzenesulfonamide and 0.017 g of N-(3-hydroxy-benzyl)-N-[4-(3-hydroxy-propyl)phenyl]-2,4,6-trimethyl-benzenesulfonamide. MS 440.2 (M+1)+

Provenance & Evidence