Benzenesulfonyl chloride, 4-chloro-3-nitro- → 4-Chloro-3-nitrobenzenesulfonic acid-n-(1-methylpiperidin-4-yl)-n-methylamide

HRID 50235

Reaktionsgleichung

Reaktionsgleichung von HRID 50235
[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]1

Komponenten

4

Edukt 2

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 5663231-Methyl-4-(methylamino)piperidine

Produkt 1

HCID 113714564-Chloro-3-nitrobenzenesulfonic acid-n-(1-methylpiperidin-4-yl)-n-methylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturewhilst cooling with ice
  2. temperaturewith cooling
  3. customevaporated to dryness
  4. additionthe residue was mixed with about 50 mL of water
  5. stirringwhilst stirring vigorously
  6. customThe crude product precipitated
  7. filtrationfiltered
  8. custompurified by column chromatography (250 g silica gel, eluant: dichloromethane with 1.5% ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-a4b92adeb6194e9899e79b37a3d3ec15
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710055B2

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