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

HRID 1633601ノート

反応式

HRID 1633601 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a390e410e4a423d91c9e48f13705ebb
出典データセット
uspto-grants-2003_01
特許番号
US06503925B1

反応ノート

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