Methylamine → N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine

HRID 334751Notes

Reaction equation

HRID 334751 reaction equation
CS(O[CH2:6][CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)(=O)=O.[CH3:16][NH2:17]>>[CH3:16][NH:17][CH2:6][CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 866302524-(Pyridin-2-yl)but-3-ynyl methanesulfonate

Product 1

HCID 66598286N-methyl-4-(pyridin-2-yl)but-3-yn-1-amineYield 39%

Conditions

Temperature
45 °C

Procedure

4-(Pyridin-2-yl)but-3-ynyl methanesulfonate (2.90 g, 12.87 mmol) was dissolved in methylamine 40% in aqueous solution (20 mL) and stirred for 3 hours under nitrogen at 45° C. The reaction mixture was cooled with ice, quenched with water and extracted with DCM. The organic phases were washed with brine, dried over MgSO4 and concentrated. The crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, DCM/MeOH: from 90/10 to 90/10 with 1% of TEA as eluent) to afford 817 mg N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine (Yield: 39%) as a brown oil

Workup

  1. temperatureThe reaction mixture was cooled with ice
  2. customquenched with water
  3. extractionextracted with DCM
  4. washThe organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, DCM/MeOH: from 90/10 to 90/10 with 1% of TEA as eluent)

Sources & evidence

ORD record
ord-cad64ee4a0524c85a4b2b7bc62bf7c84
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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