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

HRID 1651099

반응식

HRID 1651099 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 14547286alpha,alpha-Dimethyl-3-pyridinebutanamine수율 77.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0bbe340385644e0db21b6ba9594a272a
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04927826

연결된 노트

불러오는 중…