Methanesulfonyl chloride → HCID 23001031, Verbindung

HRID 397706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397706
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[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.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[NH3:1].[CH2:14]([N:11]1[CH2:12][CH2:13][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[CH:3]=2)[CH2:9][CH2:10]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 23000985HCID 23000985, Verbindung

Produkt 2

HCID 222AmmoniaHCID 23001031HCID 23001031, VerbindungAusbeute 130,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 4-(3-aminophenyl)-N-hexylpiperidine (Preparation 50, 178 mg, 0.68 mmol) in pyridine (5 ml) at room temperature under an atmosphere of nitrogen was added methanesulfonyl chloride (79 ml, 1.03 mmol) over 10 min. The resultant mixture was stirred overnight, poured onto water (10 ml) and extracted with ethyl acetate (3×10 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo at 80° C. to give the crude product which was purified by silica column chromatography, eluting with ethyl acetate:hexane:0.880 ammonia (90:9:1) to give the title compound as a pale brown oil (150 mg, 65%).

Aufarbeitung

  1. additionpoured onto water (10 ml)
  2. extractionextracted with ethyl acetate (3×10 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo at 80° C.
  5. customto give the crude product which
  6. customwas purified by silica column chromatography
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c74909ffbc4646608e0422ed6cbddb69
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610711B2

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