N-[1,1-dimethyl(3-pyridyl)butyl]-2-nitrobenzeneacetamide → alpha,alpha-Dimethyl-3-pyridinebutanamine

HRID 1651200

反応式

HRID 1651200 の反応式
[CH3:1][C:2]([NH:13]C(=O)CC1C=CC=CC=1[N+]([O-])=O)([CH3:12])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:1][C:2]([CH3:12])([NH2:13])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1

参加物

5

反応物 2

HCID 14347488N-[1,1-dimethyl(3-pyridyl)butyl]-2-nitrobenzeneacetamideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 14547286alpha,alpha-Dimethyl-3-pyridinebutanamine収率 77.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

A solution of 35.2 g of N-[1,1-dimethyl-4-(3-pyridyl)butyl]-2-nitrobenzeneacetamide in 250 mL of acetic acid was hydrogenated over 3.5 g of 10% Pd/C at atmospheric pressure and ambient temperature. The reaction was exothermic and stopped abruptly after the uptake of the theoretical amount of hydrogen (7.5 L). The catalyst was removed by filtration and the filtrate was heated at reflux for 90 minutes. After the solution was cooled, 10 mL of conc. HCl was added and the solvent was removed under reduced pressure. The residue was taken up in 1 L of water and extracted with ethyl acetate (4×200 mL) to remove the byproduct, oxindole. The aqueous layer was basified with 10N NaOH and extracted with dichloromethane to give, after evaporation of the dried (K2CO3) extracts 15 g of product. The material was distilled on a Kugelrohr apparatus (95° C.; 0.1 mm) to yield 14.3 g of alpha,alpha-dimethyl-3-pyridinebutanamine.

後処理

  1. customThe catalyst was removed by filtration
  2. temperaturethe filtrate was heated
  3. temperatureat reflux for 90 minutes
  4. temperatureAfter the solution was cooled
  5. addition10 mL of conc. HCl was added
  6. customthe solvent was removed under reduced pressure
  7. extractionextracted with ethyl acetate (4×200 mL)
  8. customto remove the byproduct, oxindole
  9. extractionextracted with dichloromethane
  10. customto give
  11. customafter evaporation of the
  12. dry with materialdried (K2CO3)
  13. distillationThe material was distilled on a Kugelrohr apparatus (95° C.; 0.1 mm)

出典と根拠

ORDレコード
ord-4c0a2ba9e70c47b28bbffcd679e59c87
出典データセット
uspto-grants-1990_05
特許番号
US04927838

関連ノート

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