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

HRID 2232137Notes

Reaction equation

HRID 2232137 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9e37b18a27f346aba59e20a40f57fc69
Source dataset
uspto-grants-1988_11
Patent number
US04786646

Reaction notes

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