Potassium Iodide → HCID 18700234, compound

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Reaction Steps

A solution of 5-methyl-spiro[isobenzofuran-1(3H),4'-piperidine] (4 g), 1,6-dibromo-hexane (2.2 g), finely powdered potassium carbonate (2.7 g) and a crystal of potassium iodide in MIBK (150 ml) was refluxed for 4 h. Inorganic salts were filtered off and MIBK evaporated. Column chromatography on silica gel (eluted with ethyl acetate/ethanol/triethylamine 75:25:4) gave the pure title compound 11a. Yield 1.0 g. Mp 113°-116° C. (recrystallized from 2-propyl ether). 1H NMR (CDCl3)δ1.30-1.45 (m,4 H), 1.50-1.65 (m,4 H), 1.80 (d,4 H), 2.00 (dt,4 H), 2.35 (s,6 H), 2.45-2.50 (m,8 H). 2.85 (broad d,4 H), 5.05 (s, 4 H), 6.95-7.10 (m,6H).

Provenance & Evidence