1-(2-(4-Nitrophenoxy)ethyl)pyrrolidine → 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline

HRID 1827510

Reaktionsgleichung

Reaktionsgleichung von HRID 1827510
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].C(OCC)(=O)C>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:17][CH:16]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

4

Edukt 1

HCID 4198581-(2-(4-Nitrophenoxy)ethyl)pyrrolidine

Produkt 1

HCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)anilineAusbeute 198,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Two identical reactions were set up side-by-side as follows. To a mixture of 1-[2-(4-nitro-phenoxy)-ethyl]-pyrrolidine (17.61 g, 74.5 mmol) and 5% palladium on carbon (2.0 g) was added 125 mL of ethyl acetate. The reaction mixture was hydrogenated at 45 psi at room temperature for 3 hr. The mixture was filtered through diatomaceous earth under nitrogen, and the filter cake was washed with ethyl acetate and methanol. The combined filtrates from both reactions were concentrated to yield 30.46 g (99%) of the title compound. MS 207.2 (M+1)+

Aufarbeitung

  1. filtrationThe mixture was filtered through diatomaceous earth under nitrogen
  2. washthe filter cake was washed with ethyl acetate and methanol
  3. concentrationThe combined filtrates from both reactions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d624c948539946008b790b700aadc061
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053212B2

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