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Methanesulfonyl chloride → 4-Ethyl-N-hexyl-4-(3-methanesulfonylaminophenyl)piperidine

HRID 397710
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 397710
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:20][CH3:21])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[NH3:1].[CH2:20]([C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:23]([CH3:22])(=[O:25])=[O:24])[CH:3]=2)[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]1)[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 230009254-(3-aminophenyl)-4-ethyl-N-hexylpiperidine

Produkt 2

HCID 222AmmoniaHCID 230009654-Ethyl-N-hexyl-4-(3-methanesulfonylaminophenyl)piperidineAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To 4-(3-aminophenyl)-4-ethyl-N-hexylpiperidine (Preparation 64, 50.0 mg, 0.174 mmol) in anhydrous pyridine (4 ml) under nitrogen at 0° C. was added methanesulfonyl chloride (0.2 ml, 1.18 mmol). The solution was stirred at room temperature for 48 h. Ice (5 g) was added and, after 30 min, the reaction mixture was extracted with dichloromethane (10 ml). The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give the crude product which was purified by silica (5 g) column chromatography, eluting with ethyl acetate:hexane:0.880 ammonia (40:60:1), then ethyl acetate:0.880 ammonia (100:1) and then methanol:ethyl acetate:0.880 ammonia (10:89:1) to give the title compound as an oil (20 mg, 29%).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with dichloromethane (10 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product which
  7. customwas purified by silica (5 g) column chromatography
  8. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bc32e551ea1046af9fec9947b25d66ad
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06610711B2

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