Ethanol → HCID 18706915, compound

Participants

Reaction Steps

2-(4-Benzyloxyphenyl)-1-ethyl-7-hydroxymethylpyrrolo[2,1,5-cd]indolizine (0.5 g, 1.3 mmol) was dissolved in 20 ml of dry dimethylsulfoxide under a nitrogen atmosphere. Sodium hydride (100%) (136 mg, 5.7 mmol) was added in portions and stirring was continued for ten minutes. 1-(2-Chloroethyl)pyrrolidine hydrochloride (0.33 g, 1.94 mmol) was added, and the solution was stirred for 4 hours. Ethanol (2 ml) was added dropwise, and the reaction mixture was diluted with 50 ml of water, 50 ml of diethyl ether and 50 ml of brine. The organic material was extracted into diethyl ether (2×50 ml), and the combined organic layers were washed with 3×50 ml of water, 25 ML of brine, dried overmagnesium sulfate, treated with decolourising charcoal and filtered through celite. The solvent was evaporated and the crude product was purified by column chromatography over silica gel 60, using 10% of methanol in dichloromethane as the eluent to afford 0.63 g (100%) of 2-(4-benzyloxyphenyl)-1-ethyl-7-((2-pyrrolidinoethoxy)methyl)pyrrolo[2,1,5-cd]indolizine as a yellow oil. 1H--NMR (CDCl3, 200 MHz) δ: 1.44 (t, 3 H); 1.82 (m, 4 H); 2.70 (m, 4 H); 2.85 (t, 2 H); 3.29 (q, 2 H); 3.82 (t, 2 H); 5.19 (s, 2 H); 5.24 (s, 2 H); 7.11-7.24 (m, 3 H); 7.31-7.60 (m, 6 H); 7.65-7.79 (m, 3 H); 7.89 (d, 1 H).

Provenance & Evidence