Sodium Hydroxide → 4-(4-Methylsulfonylaminobenzoyl)piperidine
Reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[OH-].[Na+]>>[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:19][CH:20]=1)(=[O:4])=[O:5]Participants
Procedure
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.
Workup
- filtrationThe formed crystals were filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-def3a7968ac14541bc37a05158aae8e9
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05118689
Reaction notes
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