Triethylamine → (E)-N-Methyl-N-[4-(3-aminophenyl)-3-buten-1-yl]benzamide

HRID 1250244Notes

Reaction equation

HRID 1250244 reaction equation
[CH3:1][N:2]([CH2:11][CH2:12][CH:13]=[CH2:14])[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(N(CC)CC)C>O.C(Cl)(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][N:2]([CH2:11][CH2:12]/[CH:13]=[CH:14]/[C:16]1[CH:22]=[CH:21][CH:20]=[C:18]([NH2:19])[CH:17]=1)[C:3](=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 122713-IodoanilineHCID 10559557N-Methyl-N-(3-buten-1-yl)benzamide

Product 1

HCID 15549897(E)-N-Methyl-N-[4-(3-aminophenyl)-3-buten-1-yl]benzamideYield 112.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
107.5 °C

Procedure

Under a nitrogen atmosphere, a mixture of N-methyl-N-(3-buten-1-yl)benzamide (2.15 g, 11.36 mmol), 3-iodoaniline (2.49 g, 11.36 mmol, Aldrich Chemical Company), palladium(II) acetate (25.5 mg, 0.11 mmol), and triethylamine (2.30 g, 22.70 mmol) was stirred and heated under reflux at 105-110° C. (oil bath temperature) for 52 h. The dark-brown solution was allowed to cool to ambient temperature and was diluted with water (20 mL) and CHCl3 (40 mL). The water layer was separated and extracted with CHCl3 (2×10 mL). The combined CHCl3 extracts were washed with saturated NaCl solution (10 mL), dried (CHCl3), filtered, and concentrated by rotary evaporation. Further drying under high vacuum (0.3 mm Hg) for 15 h produced a viscous, brown oil (3.59 g). The crude material was purified by column chromatography on silica gel (155.5 g, 4.0 cm i.d.×60.5 cm column) eluting with EtOAc (25→67%, v/v) in CHCl3. Fractions containing the product (Rf 0.34 in EtOAc-CHCl3, 1:1, v/v) were combined, concentrated by rotary evaporation, and vacuum dried at 45° C. for 15 h to give 1.60 g (50.2%) of an amber oil.

Workup

  1. temperatureheated
  2. temperatureto cool to ambient temperature
  3. customThe water layer was separated
  4. extractionextracted with CHCl3 (2×10 mL)
  5. washThe combined CHCl3 extracts were washed with saturated NaCl solution (10 mL)
  6. dry with materialdried (CHCl3)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customFurther drying under high vacuum (0.3 mm Hg) for 15 h

Sources & evidence

ORD record
ord-b4c3173b21b04f4bbb0254ef333b748b
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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