Potassium Iodide → 1-[2-[4-[1-(4-Fluorophenyl)-5-(2-methyltetrazol-5-yl)-1H-indol-3-yl]-1,2,3,6-tetrahydropyridin-1-yl]ethyl]-2-imidazolidinone

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A mixture of 1-(4-fluorophenyl)-5-(2-methyl-5-tetrazolyl)-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (21a) (4 g), 1-(2-chloroethyl)imidazolidin-2-one (1.8 g), potassium carbonate (2.1 g) and potassium iodide (0.5 g) in MIBK (80 mL) was boiled at reflux for 20 hours. After cooling, inorganic salts were filtered off and the solvent evaporated in vacuo. The title compound crystallised from ethyl acetate. Yield 3.0 g. Mp 201-203° C. 1H NMR (CDCl3): δ 2.60-2.70 (m, 4H), 2.80 (t, 2H), 3.30 (broad s, 2H), 3.35-3.45 (m, 4H), 3.55 (t, 2H), 4.40 (s, 3H), 4.65 (s, 1H), 6.35 (broad s, 1H), 7.20 (t, 2H), 7.25 (s, 1H), 7.40-7.50 (m, 3H), 7.95 (d, 1H), 8.25 (s, 1H); MS m/z (%): 487 (MH+, 12), 142 (49), 113 (100).

Provenance & Evidence