Diethylamine → HCID 9924451, compound

Participants

Reaction Steps

A solution of 2.5 g (0.008 mole) of 2-chloro-1-[4(2-naphthalenoyl)-1-methyl-1H-pyrrol-2-yl]ethanone and 2.5 mL (0.024 mole) of diethylamine was refluxed for 3 hr in 50 mL of EtOH. After cooling, the solvent was evaporated in vacuo. The residue was chromatographed on silica gel (90:10:1 CH2Cl2:MeOH:NH4OH). The resulting oil was treated with ethereal HCl in EtOH. The resulting gum was converted to the free base by partitioning between Et2O/NaHCO3. This was again chromatographed on silica gel (90:10:1 CH2Cl2:MeOH:NH4OH). The resulting oil was converted to the fumarate salt in 2-PrOH/EtOH. The solid was filtered to give 0.76 g (27%) of Compound 1. mp 130-132° C. CIMS m/z=349 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.4 (Ar, 1H); 8.15-8.0 (Ar, 4H); 7.85 (Ar, 1H); 7.7-7.6 (Ar, 2H); 7.2 (Ar, 1H); 6.6 (s, 2H); 4.0 (s, 3H); 3.7 (s, 2H); 2.6 (q, 4H); 1.0 (t, 6H). Anal calc'd for: C22H24N2O2.C4H4O40.33H2O: C, 66.40; H, 6.14; N, 5.96. Found: C, 66.38; H, 6.43; N, 5.73, KF water 1.22.

Provenance & Evidence