1-N-Phenyl-piperidin-4-one

Uses

1-Phenylpiperidin-4-one is a reagent used in the preparation of isoteric N-arylpiperazine as dihydropyridine NPY1 receptor antagonists.

Synthesis

The compound (CAS: 198649-62-6) was dissolved in ethanol (60 mL), 2M hydrochloric acid (15 mL) was added and the reaction was heated to reflux for 5 hours. Upon completion of the reaction, the reaction solution was neutralized by adding aqueous sodium bicarbonate to the reaction solution, followed by extraction of the organic phase with ethyl acetate. The organic phase was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (Moritex Corporation, eluent: hexane/ethyl acetate=5/1). Fractions with an Rf value of 0.40 were collected and confirmed by thin layer chromatography and concentrated under reduced pressure to give 1-N-phenyl-1-piperidin-4-one (6.1 g, 35 mmol) as a colorless oil (quantitative yield). Mass spectrum (MS) m/z: 176 (M + H)+.

References

[1] Patent: US2011/112103, 2011, A1. Location in patent: Page/Page column 23
[2] Patent: WO2010/81851, 2010, A1. Location in patent: Page/Page column 15; 16
[3] Patent: WO2013/6408, 2013, A1. Location in patent: Page/Page column 63
[4] Tetrahedron Letters, 2007, vol. 48, # 23, p. 4097 - 4099
[5] Patent: CN105985355, 2016, A. Location in patent: Paragraph 0639; 0640; 0641; 0642