2-Nitroimidazole → 4[(2-nitro-1H-imidazol-1-yl)methyl]-1-piperidinecarboxaldehyde

HRID 364706

반응식

HRID 364706 반응식
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH:19]=[O:20])[CH2:15][CH2:14]1>CN(C)C=O>[N+:1]([C:4]1[N:5]([CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH:19]=[O:20])[CH2:15][CH2:14]2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 107012-NitroimidazoleHCID 24758Sodium hydrideHCID 19812293N-Formyl-4-bromomethylpiperidine

생성물 1

HCID 202397474[(2-nitro-1H-imidazol-1-yl)methyl]-1-piperidinecarboxaldehyde수율 25.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

The mixture of 2-nitroimidazole (4.5 g, 40 mM) and 50% by weight NaH in mineral oil (1.92 g, 41 mM) in dimethylformamide (40 ml) was stirred at room temperature for 1/2 hr. A solution of 4-bromomethyl-1-piperidinecarboxaldehyde (8.3 g, 40 mM) in dimethylformamide (10 ml) was added to the above mixture and heated at 120° C. for 1/2 hr. After the reaction, solvent was removed in vacuo and water (50 ml) was added and the mixture was extracted with ethylacetate (2×75 ml). The extracts, dried over Na2SO4 was stripped to dryness which was then purified on silica gel column, eluted with 5% volume MeOH-95% volume CH2Cl2, to give 4[(2-nitro-1H-imidazol-1-yl)methyl]-1-piperidinecarboxaldehyde (2.4 g, 10 mL) in 25% yield.

후처리

  1. temperatureheated at 120° C. for 1/2 hr
  2. customAfter the reaction, solvent
  3. customwas removed in vacuo and water (50 ml)
  4. additionwas added
  5. extractionthe mixture was extracted with ethylacetate (2×75 ml)
  6. dry with materialThe extracts, dried over Na2SO4
  7. customwas then purified on silica gel column
  8. washeluted with 5% volume MeOH-95% volume CH2Cl2

출처 및 근거

ORD 기록
ord-8184314ca6104f8194cbddc12b4ae174
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605744

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