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2-Methylimidazole → 4-[3-(2-methyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde

HRID 1388408
ノート
印刷プレビュー

反応式

HRID 1388408 の反応式
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH:19]=[O:20])[CH2:15][CH2:14]1>CN(C)C=O>[CH3:1][C:2]1[N:3]([CH2:10][CH2:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([CH:19]=[O:20])[CH2:17][CH2:18]2)[CH:4]=[CH:5][N:6]=1
参加物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 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 202397684-(3-Bromopropyl)-1-piperidinecarboxaldehyde

生成物 1

HCID 202397824-[3-(2-methyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A mixture of 2-methylimidazole (2 g, 0.025 M) and sodium hydride (1.2 g, 50% in mineral oil, 0.025 M) in dimethylformamide (20 ml) was stirred at room temperature for 1/2 hr. The reaction mixture was then heated at 50° C. and the solution of 4(3-bromopropyl)piperidine carboxaldehyde (4.6 g, 0.02 M) in dimethylformamide (20 ml) was added slowly. After completing the addition, the reaction was heated at 50° C. for 4 hrs and then solvent was removed in vacuo. Water (80 ml) was added to the residue and the mixture was extracted with methylene chloride. The combined extracts, dried over sodium sulfate, were stripped to dryness to yield an oil. The oil was purified on silica gel column, eluted with methanol chloroform (1:9 v/v) to give 4-[3-(2-methyl-1H-imidazol-1-yl)-propyl]-1-piperidinecarboxaldehyde (3.86 g, 88% yield).

後処理

  1. temperatureThe reaction mixture was then heated at 50° C.
  2. additionthe addition
  3. temperaturethe reaction was heated at 50° C. for 4 hrs
  4. customsolvent was removed in vacuo
  5. additionWater (80 ml) was added to the residue
  6. extractionthe mixture was extracted with methylene chloride
  7. dry with materialThe combined extracts, dried over sodium sulfate
  8. customto yield an oil
  9. customThe oil was purified on silica gel column
  10. washeluted with methanol chloroform (1:9 v/v)

出典と根拠

ORDレコード
ord-2846eaa71cea4007a55a86030ff9be72
出典データセット
uspto-grants-1984_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04431653

反応ノート

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