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

HRID 1189277Notes

Reaction equation

HRID 1189277 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 hoursunder 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-2731a3d1aaf443b09898200cf7bc2478
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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