Formaldehyde → HCID 9969663, compound

Participants

Reaction Steps

A solution of 2.5 g (0.005 moles) of 1-[5-(1-naphthalenoyl)(1-methyl-1H-pyrrol-3-yl)]-1-ethanone, 1.1 g (0.0065 mole) of piperidine hydrochloride, and 1.0 g (0.0065 mole) paraformaldehyde in 50 mL of MeOH was heated at 65° C. for 48 h and stirred 72 h at room temperature, the reaction mixture was poured into 3N NaOH and extracted with Et2O. The organics were washed with water, brine and dried (Na2SO4). The solvent was evaporated in vacuo and the residue chromatographed on silica gel (95:5:0.5 CH2Cl2:MeOH:NH4OH). The resulting oil was treated with ethereal HCl to give 1.52 g (74%) of Compound 8. mp 141-143° C. CIMS m/z 375 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 8.2 (Ar, 2H); 8.1-7.95 (Ar, 2H); 7.75-7.5 (Ar, 4H); 6.85 (Ar, 1H); 4.15 (s, 3H); 3.45-3.2 (m, 6H); 2.8 (bq, 2H); 1.7 (m, 5H); 1.85 (m, 1H). Anal calc'd for: C24H26N2O2.HCl.0.4H2O: Theory: C, 68.94; H,6.70; N, 6.70. Found: C, 69.12; H, 6.55; N, 6.70; KF water 1.63.

Provenance & Evidence