2-Chloroimidazoline sulfate → 2-[4-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenyl]amino-imidazoline

HRID 993412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 993412
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(O)(O)(=O)=O.Cl[C:30]1[NH:31][CH2:32][CH2:33][N:34]=1>CC(O)C>[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:30]4[NH:34][CH2:33][CH2:32][N:31]=4)=[CH:21][CH:22]=3)[CH2:12][CH2:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 125033982-Chloroimidazoline sulfateHCID 218770334-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenylamine

Produkt 1

HCID 120943962-[4-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenyl]amino-imidazolineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(1-benzenesulfonylpiperidin-4-ylmethyl)-phenylamine (0.28 g, 0.83 mmol) and 2-chloro-2-imidazoline sulfate (0.25 g, 1.25 mmol) in 2-propanol (20 mL) was heated under reflux for 30 minutes under nitrogen atmosphere. The reaction mixture was concentrated in vacuo. The residue was basified with 10% sodium hydroxide solution and extracted with dichloromethane. The organic layer was washed with cold water and brine, dried, and solvents removed in vacuo. The residue was chromatographed on neutral aluminum oxide, eluting with 1% methanol/dichloromethane, to give 2-[4-(1-benzenesulfonylpiperidin-4-ylmethyl)-phenyl]amino-imidazoline (0.29 g, 89%) as a foam. Analysis for C21H26N4O2S.5H2O: Calc.: C, 61.89; H, 6.68; N, 13.75; Found: C, 62.00; H, 6.52; N, 13.85.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes under nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with cold water and brine
  6. customdried
  7. customsolvents removed in vacuo
  8. customThe residue was chromatographed on neutral aluminum oxide
  9. washeluting with 1% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-745f653774064be8a621b49641c8b22b
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06472536B1

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