Triethylamine → 5-Formyl-1-(3-(1-piperidinyl)phenyl)benzimidazole oxime

HRID 49815ノート

反応式

HRID 49815 の反応式
[C:1]([C:3]1[CH:23]=[CH:22][C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([N:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2].Cl.[OH:25]N.C(N(CC)CC)C>C(O)=O.O.[Ni]>[CH:1](=[N:2][OH:25])[C:3]1[CH:23]=[CH:22][C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]4)[CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1

参加物

7

反応物 3

HCID 8471Triethylamine2 回HCID 443297Hydroxyamine hydrochlorideHCID 227419085-Cyano-1-(3-(1-Piperidyl)phenyl)benzimidazole

生成物 1

HCID 867566235-Formyl-1-(3-(1-piperidinyl)phenyl)benzimidazole oxime収率 70%

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 284Formic Acid溶媒HCID 962Water溶媒2 回

実験手順

To a solution of 3a1 (3.83 g, 12.9 mmol) in a mixture of formic acid (45 ml) and water (15 ml) was added Raney Ni (2.14 g, slurry in water). The mixture was refluxed with stirring for 3 hours. After cooling the mixture was filtered through celite and the filtrate was evaporated to dryness. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate (1M). The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The concentrate was eluted through a short silica gel column with ethyl acetate. Evaporation of the solvent left 5-formyl-1-(3-(1-piperidinyl)phenyl)-benzimidazole (3.86 g, 100%) as an oil. This oil was dissolved in refluxing ethanol (15 ml). Hydroxyl amine hydrochloride (2.64 g, 38.0 mmol) and triethylamine (1.70 ml) was added and reflux was continued for 5 hours. The cooled mixture was rendered basic by addition of triethylamine. Water was added and the pricipitate was filtered off, washed with water and dried to yield 3b1 (2.89 g, 70%). M.p. 213-214° C.

後処理

  1. temperatureThe mixture was refluxed
  2. temperatureAfter cooling the mixture
  3. filtrationwas filtered through celite
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate (1M)
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe concentrate was eluted through a short silica gel column with ethyl acetate
  9. customEvaporation of the solvent
  10. waitleft 5-formyl-1-(3-(1-piperidinyl)phenyl)-benzimidazole (3.86 g, 100%) as an oil
  11. dissolutionThis oil was dissolved
  12. temperaturein refluxing ethanol (15 ml)
  13. temperaturereflux
  14. waitwas continued for 5 hours
  15. filtrationthe pricipitate was filtered off
  16. washwashed with water
  17. customdried

出典と根拠

ORDレコード
ord-6817c6f852024a4f91539f16d17fd089
出典データセット
uspto-grants-2004_03
特許番号
US06710044B2

反応ノート

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