Methylamine → (4E)-N-Methyl-5-(3-pyridyl)-4-penten-2-amine

HRID 2064279Notes

Reaction equation

HRID 2064279 reaction equation
C1(C)C=CC(S(O[CH:11]([CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH3:12])(=O)=O)=CC=1.[CH3:23][NH2:24]>C(O)C>[CH3:23][NH:24][CH:11]([CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH3:12]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 87466987(4E)-5-(3-Pyridyl)-4-pentene-2-ol p-Toluenesulfonate

Product 1

HCID 10219654(4E)-N-Methyl-5-(3-pyridyl)-4-penten-2-amineYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (4E)-5-(3-pyridyl)-4-penten-2-ol p-toluenesulfonate (5.60 g, 17.66 mmol), methylamine (100 mL, 40% solution in water), and ethyl alcohol (10 mL) was stirred at ambient temperature for 18 h. The resulting solution was extracted with chloroform (3×100 mL). The combined chloroform extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography over aluminum oxide, eluting with ethyl acetate-methanol (7:3, v/v). Selected fractions were combined and concentrated by rotary evaporation, producing an oil. Further purification by vacuum distillation furnished 1.60 g (51.6%) of a colorless oil, by 110-120° C. at 0.1 mm Hg.

Workup

  1. extractionThe resulting solution was extracted with chloroform (3×100 mL)
  2. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude product was purified by column chromatography over aluminum oxide
  6. washeluting with ethyl acetate-methanol (7:3
  7. concentrationconcentrated by rotary evaporation
  8. customproducing an oil
  9. customFurther purification
  10. distillationby vacuum distillation

Sources & evidence

ORD record
ord-cc72072ca6524ac888addca029b56f03
Source dataset
uspto-grants-2012_10
Patent number
US08288420B2

Reaction notes

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