I want to prepare N-alkyl pyrrolidine, 2-methylimidazolole and benzimidazole from alkyl bromides. but using base was not enough for this reaction. If someone has experience in that reaction, I will be grateful.
You can couple it direclty using K2CO3 in Dry DMF. Take phenol and 1.2eq k2co3 in dry dmf , cool to 0-5 degree and add other reagent (alkyl halide) slowly. after 30min get back reaction to room temperature. Monitor the reaction. This should work. Good luck.
The pyrrolidine may quaternise depending on the steric bulk of the alkylating agent.
Run an in situ Finkelstein alkylation in acetonitrile, Na2CO3 and NaI at reflux.
Alternatively, irreversible deprotonation with NaH or BuLi in THF may be worth investigating.
Take sodiumhydride add DMF as solvet then add your S.M and stirred for mose time after then add your alkyl halide and TBAI (tetrabuty ammonium iodide) as catalytic ammount. If reaction not work in RT then heated to 60-80 degrees.
Synthesis of N-alkylation of pyrrolidine, 2-methyl imidazole and benzimidazole can be achived by reacting these compds. with dimethyl sulphate OR by reacting these imidazoles alkyl halides in acetone in presence of K2CO3 or Triethyl amine.
2-methylimidazole and benzimidazole are actually quite cheap commercially and I would personally rather buy them than try to make them. As previously discussed, you will need a trifold excess of base in order to get imidazole to C-alkylate, and it will be expensive and a mess. Alkylation of pyrrolidine is not trivial and the yields are usually low, use biphasic systems, strong base and very good stirring.
dear ahmad
a simple and fast way is using microwave oven. using 1g k2co3 in 2cc DMF at 2 or 5 min you will achieve extremely converted product
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