Pyridine → 1-(4-Bromobenzoyl)-3-dimethylaminopyrrolidine

HRID 1176061

Reaktionsgleichung

Reaktionsgleichung von HRID 1176061
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:17][N:18]([CH3:24])[CH:19]1[CH2:23][CH2:22][NH:21][CH2:20]1>C(Cl)Cl.CCOCC>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:21]2[CH2:22][CH2:23][CH:19]([N:18]([CH3:24])[CH3:17])[CH2:20]2)=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 685154-Bromobenzoyl chlorideHCID 27585193-(Dimethylamino)pyrrolidine

Produkt 1

HCID 590120191-(4-Bromobenzoyl)-3-dimethylaminopyrrolidineAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromobenzoyl chloride (2.2 g, 10 mmol) and pyridine (1 mLl) in CH2Cl2 at 0° C. is added 3-(dimethylamino)pyrrolidine (1.14 mL, 10 mmol). The reaction is stirred at room temperature for 2 h, diluted with ether and filtered. The filtercake is washed with ether, treated with 0.1 N sodium hydroxide, stirred and filtered. This filtercake is washed with ether and recrystallized from petroleum ether to give 1-(4-bromobenzoyl)-3-dimethylaminopyrrolidine as a white powder (1.5 g), identified by NMR analysis.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtercake is washed with ether
  3. additiontreated with 0.1 N sodium hydroxide
  4. stirringstirred
  5. filtrationfiltered
  6. washThis filtercake is washed with ether
  7. customrecrystallized from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-a7c07cbf29ab4d4294af5b23e3f79c8e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842715B2

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