Sodium Iodide → 1-[N-(1-Azabicyclo[3.3.0]octan-5-yl)methyl-N-ethylamino]-4-nitronaphthalene

HRID 260920

Reaktionsgleichung

Reaktionsgleichung von HRID 260920
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[CH2:15]([NH:17][CH2:18][C:19]12[CH2:26][CH2:25][CH2:24][N:23]1[CH2:22][CH2:21][CH2:20]2)[CH3:16].[I-].[Na+].[OH-].[Na+]>N1C=CC=CC=1>[N:23]12[CH2:24][CH2:25][CH2:26][C:19]1([CH2:18][N:17]([C:2]1[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1)[CH2:15][CH3:16])[CH2:20][CH2:21][CH2:22]2

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 3127191-Chloro-4-nitronaphthaleneHCID 10749640HCID 10749640, Verbindung

Produkt 1

HCID 106170711-[N-(1-Azabicyclo[3.3.0]octan-5-yl)methyl-N-ethylamino]-4-nitronaphthaleneAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1-Chloro-4-nitronaphthalene (2.00 g, 9.63 mmol), 5-ethylaminomethyl-1-azabicyclo[3.3.0]octane (3.24 g, 19.3 mmol) and sodium iodide (580 mg) were added into anhydrous pyridine (20.0 ml) to react the mixture in a sealed tube for 20 hours at 190° C. After addition of aqueous sodium hydroxide solution subsequent to concentration in vacuo, the reaction mixture was extracted by ethyl acetate, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by column chromatography to afford the desired compound (1.00 g, 30.6%), as a yellow liquid.

Aufarbeitung

  1. customto react the mixture in a sealed tube for 20 hours at 190° C
  2. concentrationsubsequent to concentration in vacuo
  3. extractionthe reaction mixture was extracted by ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6e6833ec92c34b308874877b0333b085
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530138

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