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

HRID 993409

Reaktionsgleichung

Reaktionsgleichung von HRID 993409
[CH:1]([NH:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].S(O)(O)(=O)=O.Cl[C:27]1[NH:28][CH2:29][CH2:30][N:31]=1>CC(O)C>[CH:1]([NH:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:27]3[NH:31][CH2:30][CH2:29][N:28]=3)=[CH:18][CH:19]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 125033982-Chloroimidazoline sulfateHCID 218768574-(1-Isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine

Produkt 1

HCID 218768082-[4-(1-Isopropylaminocarbonylpiperidin-4-ylmethyl)-phenyl]amino-imidazolineAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine (0.64 g, 2.31 mmol) and 2-chloro-2-imidazoline sulfate (0.70 g, 3.47 mmol) in 2-propanol (20 mL) was heated under reflux for 30 minutes. The reaction mixture was concentrated in vacuo. The residue was diluted with water, basified with 10% sodium hydroxide solution and extracted into dichloromethane. The organic layer was washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The crude product was chromatographed on neutral aluminum oxide, eluting with 5% methanol/dichloromethane, and crystallized from ethyl acetate containing some ethanol, to give 2-[4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenyl]amino-imidazoline (0.47 g, 59%) as a white solid, m.p. 191-192° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted into dichloromethane
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was chromatographed on neutral aluminum oxide
  10. washeluting with 5% methanol/dichloromethane
  11. customcrystallized from ethyl acetate containing some ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f4f612df8b3a42efa398b3f6b28444f6
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06472536B1

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