Pyrrolidine → 1-[(3-Nitrophenyl)methyl]pyrrolidine

HRID 1633594

Reaktionsgleichung

Reaktionsgleichung von HRID 1633594
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Produkt 1

HCID 7828801-[(3-Nitrophenyl)methyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-nitrobenzylbromide (3 g, 13.9 mmol) in anhydrous THF (30 ml) was added a solution of pyrrolidine (2.3 ml, 27.8 mmol) in anhydrous THF (10 ml) dropwise with stirring. Following the addition the mixture was stirred at ambient temperature overnight. The reaction mixture was filtered. The filter cake was washed with a small volume of anhydrous THF and the filtrate was concentrated to leave the intermediate 1-(3-nitrobenzyl)pyrrolidine as an oil. This oil was dissolved in methanol (50 ml) and three equivalents of both ammonium chloride and sodium sulfide nonahydrate were added. The mixture was heated to reflux for 2 hours. After cooling the mixture was filtered. The filtercake was washed with methanol and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and dried over sodium sulfate. Filtration and evaporation of solvent left 2i quantitatively as yellow crystals.

Aufarbeitung

  1. additionthe addition the mixture
  2. stirringwas stirred at ambient temperature overnight
  3. filtrationThe reaction mixture was filtered
  4. washThe filter cake was washed with a small volume of anhydrous THF
  5. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-f589340123f042b6836598ac09fedd47
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503925B1

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