2,4-Dimethoxybenzaldehyde → N-(2,4-dimethoxybenzyl)prop-2-yn-1-amine

HRID 2096277Notes

Reaction equation

HRID 2096277 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH2:13]([NH2:16])[C:14]#[CH:15].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:16][CH2:13][C:14]#[CH:15]

Participants

5

Reactant 3

HCID 691752,4-DimethoxybenzaldehydeHCID 239041PropargylamineHCID 4311764Sodium borohydride

Product 1

HCID 28419238N-(2,4-dimethoxybenzyl)prop-2-yn-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4-dimethoxybenzaldehyde (2.5 g, 15.06 mmol) in methanol (100 ml) was added prop-2-yn-1-amine (1.0 g, 18.18 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 hours, and then cooled to 0° C. NaBH4 (1.0 g, 26.32 mmol) was then added in portions over 15 minutes. The mixture was warmed up and stirred at room temperature for an additional 2 hours. The reaction was quenched with brine (200 mL), and partitioned between brine and ethyl acetate. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound which was used in next step without further purification. 1H NMR (400 MHz, dimethylsulfoxide-d6): δ 2.07 (br s, 1H), 3.04 (s, 1H), 3.27 (s, 2H), 3.63 (s, 2H), 3.74 (s, 3H), 3.76 (s, 3H), 6.46 (d, J=8.0 Hz, 1H), 6.52 (s, 1H), 7.15 (d, J=8.4 Hz, 1H).

Workup

  1. temperaturecooled to 0° C
  2. temperatureThe mixture was warmed up
  3. stirringstirred at room temperature for an additional 2 hours
  4. customThe reaction was quenched with brine (200 mL)
  5. custompartitioned between brine and ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2c9a6fa366c84fe796aaceb33f95c8d9
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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