Reaktion #7045

Reaktionsgleichung

1-(2-chloroethyl)-pyrrolidine hydrochloride

Potassium carbonate

sodium iodide

3-methyl-2-nitrophenol

1-(2-chloroethyl)-pyrrolidine hydrochloride

potassium carbonate

→

1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine

Ausbeute 69.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   TemperaturAfter an additional hour of reflux
3. 3
   Waschenwas washed with sequentially with water (1×100 mL) and brine (1×100 mL.) The combined organic fractions
4. 4
   Sonstigespontaneously crystallized
5. 5
   Sonstigethe solid was purified by flash chromatography (5% MeOH in CH2Cl2)

Vorschrift

Potassium carbonate (34.9 g., 252 mmol) and sodium iodide (1.0 g., 6.5 mmol) were added to a solution of 3-methyl-2-nitrophenol (10 g., 65.3 mmol). With stirring, 1-(2-chloroethyl)-pyrrolidine hydrochloride (16.65 g., 98 mmol) was added portion-wise to the solution. The reaction mixture was refluxed for 15 hours, at which time 1-(2-chloroethyl)-pyrrolidine hydrochloride (8.5 g., 50 mmol) and potassium carbonate (18 g., 130 mmol) were added. After an additional hour of reflux, the reaction mixture was allowed to cool to room temperature and was washed with sequentially with water (1×100 mL) and brine (1×100 mL.) The combined organic fractions spontaneously crystallized, and the solid was purified by flash chromatography (5% MeOH in CH2Cl2) to give 1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine (10.291 g., 69%). MS: 251 (M+H)+

Quelle