Dimethylformamide → p-Cyclopropanoyl N,N,N-Trimethylanilinium Iodide

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Reaction Steps

p-N,N-Dimethylaminophenyl cyclopropyl ketone (186.50 mg, 0.99 mmol) is added to 2 ml of dimethylformamide (DMF). Methyl iodide (0.24 g, 7.4 mmol) is added to the solution, the flask stoppered and the solution stirred for 18 hrs. Ethyl acetate is added to the flask to precipitate the product and the solution is filtered. The precipitate is washed with ethyl acetate, ether and chloroform. The precipitate is then dissolved in a minimal amount of methanol and filtered. Ether is added to the filtrate to precipitate the product. The product is filtered and washed with ether and dried. This yielded 2B as a white crystalline solid (56.25 mg, 17.2% yield); m.p. >280° C.; IR (KBr):1660 cm-1 (C=O): NMR (CD3CN) δ:1.15 (d, 4H); 2.60 (m, 1H ); 3.61 (s, 9H); 7.93 (d, 2H); 8.24 (d, 2H); mass spectrum m/e=189 (M-CH3I). Calculated for C13H18ION:C, 47.14; H, 5.49; I, 38.31, N, 4.23. Found: C, 45.60; H, 5.49; I 38.91; N, 4.50. HPLC analysis of the product show that no cyclopropyl p-fluorophenyl ketone is present in the final product.

Provenance & Evidence