Sodium hydride → HCID 18706986, compound

Participants

Reaction Steps

2-(4-Benzyloxyphenyl)-1-ethyl-4-hydroxymethylpyrrolo[2,1,5-cd]indolizine (0.88 g, 1.26 mmol) was dissolved in 40 ml of dry dimethylformamide under a nitrogen atmosphere. Sodium hydride (80% in oil) (0.24 g, 8.0 mmol) and potassium tert-butoxide (0.1 g, 0.9 mmol) was added in portions and stirring was continued for ten minutes. 1-(2-chloroethyl)piperidine hydrochloride (0.74 g, 4 mmol) was added, and the solution was stirred for four hours. Ethanol (10 ml) was added dropwise, and the reaction mixture was diluted with 200 ml of water. The organic material was extracted into toluene (3×50 ml), and the combined organic layers were dried over magnesium sulfate. 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 0.505 g (81%) of 2-(4-benzyloxyphenyl)-1-ethyl-4-((2-piperidinoethoxy)methyl)pyrrolo[2,1,5-cd]indolizine as a yellow oil. MS(SP): m/z 492 (M+). 1H-NMR (CDCl3, 300 MHz) δ: 1.35-1.50 (m, 5H); 1.68 (m, 4H); 2.63 (m, 4H); 2.76 (t, 2H); 3.23 (q, 2H); 3.79 (t, 2H); 5.01 (s, 2H); 5.12 (s, 2H); 7.13 (d, 2H); 7.30-7.50 (m, 5H); 7.52 (s, 1H); 7.62 (t, 1H); 7.70 (d, 2H); 7.88 (d, 1H); 7.97 (d, 1H).

Provenance & Evidence