Benzenesulfonyl chloride, 4-chloro-3-nitro- → 4-Chloro-3-nitrobenzenesulfonic acid-n-(1-methylpiperidin-4-yl)-n-methylamide
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH3:9])[CH2:4][CH2:3]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>N1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]([CH3:9])[S:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[C:12]([N+:21]([O-:23])=[O:22])[CH:13]=2)(=[O:18])=[O:19])[CH2:4][CH2:3]1Participants
4
Procedure
To a solution of 2.2 mL (15 mmol) of 1-methyl-4-methylaminopiperidine in 60 mL pyridine, 3.8 g (15 mmol) of 4-chloro-3-nitrobenzenesulfonic acid chloride were added, in batches, whilst cooling with ice. The mixture was then stirred for two hours with cooling, then evaporated to dryness, the residue was mixed with about 50 mL of water and made alkaline with concentrated ammonia whilst stirring vigorously. The crude product precipitated was suction filtered and purified by column chromatography (250 g silica gel, eluant: dichloromethane with 1.5% ethanol). Yield: 1.6 g (31% of theory), C13H18ClN3O4S (347.8); Rf value: 0.19 (silica gel; dichloromethane/ethanol=19:1).
Workup
- temperaturewhilst cooling with ice
- temperaturewith cooling
- customevaporated to dryness
- additionthe residue was mixed with about 50 mL of water
- stirringwhilst stirring vigorously
- customThe crude product precipitated
- filtrationfiltered
- custompurified by column chromatography (250 g silica gel, eluant: dichloromethane with 1.5% ethanol)
Sources & evidence
- ORD record
- ord-a4b92adeb6194e9899e79b37a3d3ec15
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06710055B2
Reaction notes
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