Hydrochloric Acid → 1-(3-Hydroxypropyl)piperazin-2-one

Participants

Reaction Steps

Tert-butyl 4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-3-oxopiperazine-1-carboxylate (2.90 g, 7.8 mmol) in 1,4-dioxane (10 ml) was treated at room temperature with a 4N solution of HCl in 1,4-dioxane (15 ml) and the resulting solution stirred 4 hr then evaporated. The residue was taken up in a 10% methanol in dichloromethane solution (30 ml) and basified with a 7N solution of ammonia in methanol then filtered and the filtrate evaporated. The residue was purified by column chromatography on silica using increasing concentrations of methanolic ammonia in dichloromethane as eluent to give 1-(3-hydroxypropyl)piperazin-2-one (708 mg, 57%) as a colourless oil; NMR Soectrum:(CDCl3) 1.77 (quintet, 2H), 2.72 (s(br), 2H), 3.09 (t, 2H), 3.32 (t, 2H), 3.55 (m, 6H).

Provenance & Evidence