Pyridine → HCID 131726129, compound

Participants

Reaction Steps

To a solution of (intermediate 6) 2-(4-nitro-1-naphthyl)octahydropyrrolo[1,2-a]pyrazine (0.160 g, 0.54 mmol) in 10 mL THF:EtOH (20 mL,1:4) was added Raney-Ni (1.0 mL suspension in EtOH) followed by hydrazine hydrate (0.135 g, 2.70 mmol). The mixture was stirred vigorously at room temperature for 16 hours and then filtered through celite pretreated with water. The filtrate was concentrated and the residue was dissolved in CH2Cl2 (3 mL) and pyridine (0.35 mL, 3.78 mmol) and p-toluensulfonyl chloride (0.13 g, 0.54 mmol) were added to the solution. The reaction mixture was stirred at room temperature for 16 hours and then concentrated. The crude product was purified by column chromatography chromatography (SiO2, CHCl3/MeOH/NH3 9:1:0.4%) to give 0.217 g (95%) of the free base which was converted to its HCl-salt: 1H NMR (CD3OD) δ 8.21–8.14 (m, 1H), 7.97–7.93 (m, 1H), 7.58–7.47 (m, 3H), 7.43–7.37 (m, 1H), 7.25–7.10 (m, 4H), 4.12–4.02 (m, 1H), 3.80–3.0 (m, partly obscured by solvent signal, 8H), 2.45–2.10 (m, 3H), 2.35 (s, 3H), 1.87–1.75 (m, 1H); MS (posEI) m/z 421 (M+).

Provenance & Evidence