4-(Bromomethyl)benzenesulfonyl chloride → 4-[4-(Bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone

HRID 1840556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840556
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][C:16]2=[O:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Br:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([N:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)[C:16](=[O:21])[CH2:17]2)(=[O:32])=[O:31])=[CH:28][CH:29]=1

Komponenten

5

Edukt 2

HCID 27344094-(Bromomethyl)benzenesulfonyl chlorideHCID 234475144-(2-Oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 234476104-[4-(Bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinoneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (500 mg) in ethyl acetate (15 ml) and sodium bicarbonate solution (10 ml) was added at 0° C. 4-(bromomethyl)benzenesulfonyl chloride (453 mg), and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated, washed with brine, dried and concentrated, and the residue was purified with silica gel column chromatography (hexane: ethyl acetate=2:3) to give colorless crystals of 4-[4-(bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (437 mg).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was purified with silica gel column chromatography (hexane: ethyl acetate=2:3)

Quellen und Nachweise

ORD-Eintrag
ord-5e6e23d9dd0349eebda7318cbccd75b9
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680312B2

Notizen zur Reaktion

Wird geladen…