Sodium Hydroxide → 4-(4-Methylsulfonylaminobenzoyl)piperidine

Participants

Reaction Steps

10.0 g (31.4 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride was suspended in 20 ml of an aqueous solution of 1.32 g of sodium hydroxide and the suspension was stirred at room temperature for 1 h. The formed crystals were filtered, washed with water and dried to obtain 8.28 g of 4-(4-methylsulfonylaminobenzoyl)piperidine in free form. A mixture of 2.0 g (7.09 mmol) of the obtained crystals, 1.57 g of chloroethylpyrrolidine hydrochloride, 2.35 g of potassium iodide and 40 ml of dimethylformamide was stirred at 80° C. for 3 h. The reaction mixture was filtered and the filtrate was concentrated to obtain a solid residue, which was then purified according to silica gel column chromatography (chloroform: methanol:aqueous ammonia=90:9:1). 0.68 g of the purified product was converted into its dioxalate with 0.32 g of oxalic acid in ethanol. After recrystallization from methanol/ethanol, 0.40 g (yield: 10% of the intended compound was obtained.

Provenance & Evidence