I have tried the reaction condition ranging from using base K2CO3, KOH, to NaH as well varying the reaction solvent too starting from acetone, THF, DMF....Heated the reaction as well....
However in literature the reaction goes quite smoothly ...
Plz help
My suggestions: It might be worth using a phase transfer catalysts such as 18-crown-6 or TBAB. Use fine powder (mortar pestle to make a fine powder) of K2CO3/KOH/NaOH that might also help. Try drying the powdered base (organic solvent reaction) in an oven above 100 °C for a day and then use it. The procedure I used for N-alkylation of pyrrole was - To a solution of pyrrole in DMSO was added NaOH powder and sonicated for 30 mins. Then TBAB was added and stirred at room temperature for 30 min. To this 2-bromoethylamine hydrobromide in DMSO was added. Then the reaction mixture was heated at 80 °C for 18 h. Hope this helps.
You can try with NaH base with DMF solvent. This may help to you to get N-alkylation.
If the above method you not get product try with potassium tertiary butoxide or sodium methoxide base.
You have use always dry solvent for your reaction. Anhydrous DMF, Anhydrous THF.
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