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

HRID 364743
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HRID 364743 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 202397684-(3-Bromopropyl)-1-piperidinecarboxaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A mixture of 2-methylimidazole (2 g, 0.025M) and sodium hydride (1.2 g, 50% in mineral oil, 0.025M) 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, 0.02M) 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-fdf277529bcc49399e17df10221aa168
출처 데이터셋
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04605744

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