Hydrochloric Acid → 4-[{N-(2-amino5-chlorobenzoyl)glycyl}aminomethyl]piperidine

Participants

Reaction Steps

To a solution of 4-[{(N-(2-amino-5-chlorobenzoyl)glycyl)amino}methyl]-1-(tert-butoxycarbonyl)piperidine (1.63 g, 3.84 mmol) in methanol (20 mL) was added 4 N HCl in dioxane (9.5 mL). The solution was stirred at room temperature for 6 h. The reaction mixture was concentrated and 2 N aqueous NaOH solution (20 mL) was added. The mixture was extracted with dichloromethane (20 mL×3), and the combined extracts were dried over sodium sulfate, filtered and concentrated to give 4-[{(N-(2-amino-5-chlorobenzoyl)glycyl)amino}methyl]piperidine (1.19 g, 95%): 1H NMR (CDCl3, 270 MHz) δ1.10-1.76 (m, 4H), 2.55 (td, J=2.4 and 12.2 Hz, 2H), 3.00-3.10 (m, 2H), 3.17 (t, J=6.2 Hz, 2H), 3.48 (s, 2H), 4.03 (d, J=4.9 Hz, 2H), 5.50 (br. s, 2H), 6.11-6.23 (m, 1H), 6.60 (d, J=8.8 Hz, 1H), 6.85-7.02 (m, 1H), 7.15 (dd, J=2.7 and 8.8 Hz, 1H), 7.38 (d, J=2.4 Hz, 1H); ESI/MS m/e 325.2 (C15H21ClN4O2).

Provenance & Evidence