تفاعل #7045

معادلة التفاعل

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

المردود 69.0%

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)+

المصدر