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

HRID 76080

反応式

HRID 76080 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:22])[CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:12].CS(C)=O>CCOCC>[CH2:11]([O:13][C:14](=[O:22])[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH2:18][CH2:17]1)[CH3:12]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 98284'-FluoroacetophenoneHCID 2760465Ethyl 2-(piperidin-4-yl)acetate

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 3283Diethyl Ether溶媒

反応条件

温度
150 °C

実験手順

A microwave vial was charged with 4′-fluoroacetophenone (1.2 Ml, 10.4 mmol, 1.0 equiv) and 2-(piperidin-4-yl)-acetic acid ethyl ester (3.5 g, 20.7 mmol, 2.0 equiv) in 20 Ml DMSO. The homogeneous reaction was heated to 150° C. for 20 min. The cooled reaction was then diluted with ether and washed sequentially with saturated ammonium chloride, water, and brine. The organic extracts were then dried over sodium sulphate, filtered, and concentrated in vacuo. Purification by flash chromatography (10-40% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (t, J=7.07 Hz, 3H) 1.47 (d, J=12.13 Hz, 2H) 1.62 (br.s., 1H) 1.90 (d, J=12.63 Hz, 2H) 2.04-2.15 (m, J=11.18, 11.18, 7.45, 7.45, 3.79, 3.66 Hz, 1H) 2.33 (d, J=7.07 Hz, 2H) 2.57 (s, 3H) 2.97 (td, J=12.57, 2.15 Hz, 2H) 3.93 (d, J=12.88 Hz, 2H) 4.20 (q, J=7.07 Hz, 2H) 6.96 (d, J=6.82 Hz, 2H) 7.92 (d, J=9.09 Hz, 2H); (M+H)+290.1.

後処理

  1. customThe homogeneous reaction
  2. customThe cooled reaction
  3. washwashed sequentially with saturated ammonium chloride, water, and brine
  4. dry with materialThe organic extracts were then dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (10-40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-96dbcddc02ee40bf91e3618a3e3668a8
出典データセット
uspto-grants-2014_09
特許番号
US08835451B2

関連ノート

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