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

HRID 422464Notes

Reaction equation

HRID 422464 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-ee5ca62c43804095b05baaa1e9f513ec
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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