反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19](=[O:22])[CH2:20]Br)[CH3:17].C(N(CC)CC)C>C(#N)C>[CH2:16]([O:18][C:19](=[O:22])[CH2:20][N:13]1[CH2:14][CH2:15][CH:10]([C:8](=[O:9])[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:11][CH2:12]1)[CH3:17]参加物
反応条件
- 温度
- 85 °C
実験手順
To a suspension of (4-chloro-phenyl)-piperidin-4-yl-methanone (1.0 g, 3.8 mmol) and bromo-acetic acid ethyl ester (0.71 g, 4.2 mmol) in acetonitrile (10 mL) was added triethylamine (0.78 g, 7.7 mmol), the reaction mixture was stirred at 85° C. for 15 h. The reaction mixture was cooled to ambient temperature, the solvent was removed, the residue was redissolved in DCM (20 mL), washed with water (20 mL), the organic layers were then washed with brine (20 mL) and dried over Na2SO4. Purification by flash chromatography gave the title compound as a white solid (1.01 g, 3.10 mmol, 81% yield). MS (ESI) m/z 310.3 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.45 min.
後処理
- temperatureThe reaction mixture was cooled to ambient temperature
- customthe solvent was removed
- dissolutionthe residue was redissolved in DCM (20 mL)
- washwashed with water (20 mL)
- washthe organic layers were then washed with brine (20 mL)
- dry with materialdried over Na2SO4
- customPurification by flash chromatography
出典と根拠
- ORDレコード
- ord-b93deea389a9414db218e841e0a52304
- 出典データセット
- uspto-grants-2015_11
- 特許番号
- US09181266B2
関連ノート
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