Cesium carbonate → HCID 67974225、化合物

HRID 2174469ノート

反応式

HRID 2174469 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl[CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 691274-Chloro-3-nitrophenolHCID 104870044-(2-chloroethyl)piperidine

生成物 1

HCID 67974225HCID 67974225、化合物収率 56.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

4-chloro-3-nitrophenol (2.5 g, 14.4 mmol, 1 eq.) was placed in dimethylformamide (48 mL) with 4-(2-chloro-ethyl)piperidine (8 g, 43.2 mmol, 3 eq.), Cs2CO3 (33 g, 100.8 mmol, 7 eq.), KI (5.3 g, 31.7 mmol, 2.2 eq.). The reaction mixture was heated at 80° C. and stirred for 20 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with a 1% NaOH aqueous solution, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 4-(2-(4-chloro-3-nitrophenoxy)ethyl)piperidine (2.3 g, 56%).

後処理

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washThe organic phase was washed with a 1% NaOH aqueous solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-f293ecc095c44665ad213e3c7bd45480
出典データセット
uspto-grants-2015_06
特許番号
US09061999B2

反応ノート

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