Formaldehyde → 5-Chloro-1-(4-fluorophenyl)-3-[1-[2-(3-hydroxymethyl-2-imidazolidinon-1-yl)ethyl]-4-piperidyl]-1H-indole

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Reaction Conditions

Reaction Steps

To a solution of 5-chloro-1-(4-fluorophenyl)-3-[1-[2-(2-imidazolidinon-1-yl)ethyl]-4-piperidyl]-1H-indole (4.4 g) in tetrahydrofuran (25 ml) at room temperature was added dropwise a 30% aqueous solution of formaldehyde (800 mg). The mixture was heated at 50 ° C. for 2 h. Solvents were evaporated in vacuo and excess H2O was removed by evaporation with toluene. By addition of acetone the title compound crystallized. Recrystallization from acetone afforded 3.2 g of pure 5a. Mp: 118°-119 ° C. 1H NMR: δ1.85 (2H, dq), 2.05 (2H, broad d), 2.20 (2H, t), 2.60 (2H, t), 2.85 (1H, tt), 3.10 (2H, broad d), 3.40 (2H, t), 3.50 (4H), 4.80 (2H, s), 7.0-7.7 (8H).

Provenance & Evidence