4-(N-Boc-amino)piperidone may be used as a functionalization reagent for introduction of a primary and a tertiary amino group to poly(2-isopropyl-2-oxazoline. It can also be used as pharma building block. It is used in the synthesis of a piperidine-4-carboxamide CCR5 antagonist with potent anti-HIV 1-activity. It is an intermediate for the synthesis of various pharmaceutical and biologically active compounds, including inhibitors and therapeutic agents. It is used for the synthesis of diphenyl purine derivatives as peripherally selective cannabinoid receptor 1 Antagonists.
General procedure for the synthesis of 4-tert-butoxycarbonylaminopiperidine from tert-butyl (1-benzylpiperidin-4-yl)carbamate: N-butyl-1-benzylpiperidin-4-ylcarbamate (3.80 g, 13.1 mmol) was dissolved in 26 mL of methanol in a 100 mL reaction vessel. A catalytic amount of 10% palladium/carbon (Pd/C) was added. The reaction was stirred under hydrogen atmosphere for 12 hours. Upon completion of the reaction, the palladium/carbon catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography to afford 4-tert-butoxycarbonylaminopiperidine (2.64 g, 99% yield). The product was confirmed by 1H-NMR (200 MHz, CD3OD): δ 1.36 (s, 9H), 1.84-2.36 (m, 4H), 2.74 (m, 2H), 3.42 (m, 2H), 3.60 (br, 1H).LC/MS analysis showed the [M+H]+ peak as 201.
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