Ethanol → HCID 18707006, compound

Participants

Reaction Steps

5-Benzyloxy-2-(4-benzyloxyphenyl)-3-((5-chloropentyloxy)methyl)-1-ethylpyrrolo[2,1,5-cd ]indolizine (0.41 g, 0.69 mmol) was dissolved in 50 ml of dry dimethylformamide under a nitrogen atmosphere. Sodium hydride (60% in oil) (0.40 g, 10 mmol) and piperidine (0.93 g, 11mmol) was added, and the mixture was stirred at 60° for 5 days. Ethanol (10 ml) was added dropwise, and the reaction mixture was diluted with 200 ml of water. The organic material was extracted into ethyl acetate (3×100 ml), and the combined organic layers were washed with brine and dried over sodium sulfate. The solvent was evaporated and the crude produce was purified by column chromatography over silica gel 60, using 10% of methanol in dichloromethane as the eluent. Fractions containing the product were collected and crystallised from diethyl ether and dichloromethane to afford 161 mg (36%) of 5-benzyloxy-2-(4-benzyloxyphenyl)-1-ethyl-3-((5-piperidinopentyloxy)methyl)pyrrolo[2,1,5-cd ]indolizine as yellow crystals. M.p. 106-107° C. MS(SP): m/z 627 (M+1). 1H-NMR (DMSO-d6, 300 MHz) δ: 1.16-1.75 (m, 15H); 2.61-2.95 (m, 4H); 3.07 (q, 2H); 3.21-3.24 (m, 4H); 4.71 (s, 2H); 5.20 (s, 2H); 5.56 (s, 2,H); 7.30-7.64 (m, 14H); 7.99 (d, 1H).

Provenance & Evidence