Hydrochloric Acid → HCID 17823029, compound

Participants

Reaction Steps

A 4 M dioxane solution of HCl was added to a methanol (80 mL) solution of 1-benzyl-4-[N-(tert-butoxycarbonyl)glycyl]aminopiperidine (6.59 g). The resulting solution was stirred at room temperature for 2 hours and concentrated. A 2 M aqueous solution of NaOH (20 mL) was then added to the solution. The resulting mixture was extracted with dichloromethane (40 mL). The extracts were combined, dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by column chromatography (SiO2, ethyl acetate/methanol/triethylamine=85:12:3) to thereby provide 1-benzyl-4-(glycylamino)piperidine (3.91 g, 83%). 1H NMR (CDCl3, 400 MHz) δ 1.47-1.59 (m, 2H), 1.59 (br, 2H), 1.76-1.96 (m, 2H), 2.10-2.19 (m, 2H), 2.75-2.87 (m, 2H), 3.29 (s, 2H), 3.50 (s, 2H), 3.65-3.89 (m, 1H), 7.15-7.23 (m, 1H), 7.23-7.33 (m, 5H).

Provenance & Evidence