Ethanol → 5-Acetyl-1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole

HRID 324736노트

반응식

HRID 324736 반응식
[C:1]([C:4]1[CH:23]=[CH:22][C:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH2:20][N:19]([CH3:21])[CH2:18][CH2:17][CH:16]=3)[CH:10]=2)=[C:6]([N+:24]([O-])=O)[CH:5]=1)(=[O:3])[CH3:2].[CH2:27](O)C>[Pd]>[C:1]([C:4]1[CH:23]=[CH:22][C:7]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]4[CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH2:20]4)[CH:10]=3)[CH:27]=[N:24][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 702EthanolHCID 227418634-acetyl-N-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]-2-nitroaniline

생성물 1

HCID 227418345-Acetyl-1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole수율 50%

시약·촉매·용매 1

HCID 23938Palladium촉매

반응 조건

온도
80 °C

실험 절차

To a solution of 4-acetyl-N-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]-2-nitroaniline (6, Ex. 12a) (1 g, 3 mmol) in ethanol (50 ml) was added a catalytic amount of palladium on charcoal and the mixture was hydrogenated at ambient pressure over night. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. To this concentrate formic acid (10 ml) was added and the resulting solution was stirred at 80° C. over night. Excess formic acid was removed by evaporation. The residue was dissolved in water and rendered alkaline by addition of solid sodium carbonate. Extraction with ethyl acetate and treatment of the extract with activated carbon in ethanol afforded 5-acetyl-1-[3-(1-methylpiperidin-3-yl)phenyl]-benzimidazole (9) (0.5 g, 50%) as an oil. m/e 333.

후처리

  1. waitthe mixture was hydrogenated at ambient pressure over night
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo this concentrate formic acid (10 ml) was added
  5. customExcess formic acid was removed by evaporation
  6. dissolutionThe residue was dissolved in water
  7. additionby addition of solid sodium carbonate
  8. extractionExtraction with ethyl acetate and treatment of the
  9. extractionextract with activated carbon in ethanol

출처 및 근거

ORD 기록
ord-d59b78b176b14ed2bc224d08e33d3d1a
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218547B1

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