Water → [1-(4-Acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester

HRID 2262705Notes

Reaction equation

Cl.[CH2:2]([O:4][C:5](=[O:13])[CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:3].F[C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH2:2]([O:4][C:5](=[O:13])[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=2)[CH2:9][CH2:8]1)[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of piperidin-4-yl-acetic acid ethyl ester hydrochloride (24 mmol) in anhydrous DMSO (20 mL) is added 1-(4-fluoro-phenyl)-ethanone (24 mmol) and potassium carbonate (24 mmol). The resulting mixture is heated at 90° C. for 36 hr. The reaction mixture is allowed to cool to rt, poured into cold water (100 mL), and extracted with EtOAc (40 mL×3). The combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. The crude product is purified through silica gel flash chromatography (hexane/ethyl acetate 2:1) to give the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.86 (2H, d), 6.85 (2H, d), 4.15 (2H, q), 3.89 (2H, br, d), 2.90 (2H, dt), 2.51 (3H, s), 2.27 (2H, d), 2.04 (1H, m), 1.83 (2H, br, d), 1.38 (2H, dt), 1.27 (3H, t); LC-MS (M+1): 290.

Workup

temperatureto cool to rt
extractionextracted with EtOAc (40 mL×3)
washThe combined organic layers are washed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe crude product is purified through silica gel flash chromatography (hexane/ethyl acetate 2:1)

Sources & evidence

ORD record: ord-3148f61b56fa469eae329d04404b48eb
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851474B2

Reaction notes

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