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

HRID 2262705ノート

反応式

HRID 2262705 の反応式
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]

参加物

6

反応物 4

HCID 962WaterHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 45358839Piperidin-4-yl-acetic acid ethyl ester hydrochloride

生成物 1

HCID 57442326[1-(4-Acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-3148f61b56fa469eae329d04404b48eb
出典データセット
uspto-grants-2010_12
特許番号
US07851474B2

反応ノート

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