Methyl iodide → 1-Methyl-3-{N-[beta-(4-pivalyloxyphenyl)ethyl]}carbamoylpyridinium iodide

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Reaction Steps

To a solution of 1.63 g (5 mmol) of the product of Example 26 in 10 ml of acetone, 1.41 g (10 mmol) methyl iodide were added and the mixture was refluxed overnight while stirring. The acetone layer was separated by decantation and the yellowish, oily residue was crystallized from methanol/ether. Yield, 1.94 g (83%), m.p. 155°-157° C. PMR (D2O) δ 9.16-8.00 (m, 4H, C5H4N+), 7.33-6.83 (m, 4H, C6H4), 4.40 (s, 3H, N+ --CH3), 3.5 (t, 2H, J=7 Hz, ##STR1539## 2.90 (t, 2H, J=7 Hz, CH2), 1.30 (s, 9H, C--(CH3)3). Anal. (C20H25N2O3I) C, H, N.

Provenance & Evidence