Diisopropylethylamine → 4-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one

HRID 730827ノート

反応式

HRID 730827 の反応式
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl[C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.O>[F:16][C:15]([F:18])([F:17])[C:14]1[C:9]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)=[N:10][CH:11]=[CH:12][CH:13]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

生成物 1

HCID 471744384-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of piperazin-2-one (4.85 g, 48.47 mmol, Avocado Research), 2-chloro-3-trifluoromethyl-pyridine (8.8 g, 48.47 mmol, TCI America) and diisopropylethylamine (11 mL, 58.16 mmol, Aldrich) in DMSO (160 mL) was heated at 120° C. for 16 h. The mixture was cooled to room temperature, diluted with H2O (500 mL) and extracted with EtOAc (2×500 mL). The combined organic extracts were dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with dichloromethane/MeOH (15:1) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 206 (M+1).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×500 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane/MeOH (15:1)

出典と根拠

ORDレコード
ord-2173b642f10942b68982dc1ad14f91f5
出典データセット
uspto-grants-2009_09
特許番号
US07582761B2

反応ノート

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