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Benzyl Bromide → 1-Benzyl-piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide

HRID 1020034
ノート
印刷プレビュー

反応式

HRID 1020034 の反応式
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[CH:11]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([CH:19]2[CH2:24][CH2:23][N:22]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:21][CH2:20]2)=[O:18])[CH:11]=1)[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59508999Piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide

生成物 1

HCID 595090931-Benzyl-piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide収率 21.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #1A) (0.60 g, 1.84 mmol) and potassium carbonate (0.25 g, 1.8 mmol) in DMF (40 mL) was added benzyl bromide (0.31 g, 0.22 ml, 1.84 mmol) at room temperature. The reaction mixture was heated at 60° C. for one hour and the progress of the reaction was monitored by TLC. The mixture was poured onto ice water and extracted with ethyl acetate (3×100 ml). The organic layers were separated, combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was triturated with dry diethyl ether and the solid was filtered to obtain 1-benzyl-piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #5A) (0.165 g. 21%) as a yellow solid.

後処理

  1. additionThe mixture was poured onto ice water
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. customThe organic layers were separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was triturated with dry diethyl ether
  8. filtrationthe solid was filtered

出典と根拠

ORDレコード
ord-c93ff18cf53d470b9e709751fdb4a4f9
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08716296B2

反応ノート

読み込み中…

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