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

HRID 2096271Notes

Reaction equation

HRID 2096271 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 (2.51 g, 15.13 mmol) in methanol (100 ml) was added prop-2-yn-1-amine (1.0 g, 18.16 mmol). The reaction mixture was stirred at room temperature for 1.5 hours, and cooled to 0° C. NaBH4 (1.0 g, 27.2 mmol) was added in portions over 15 minutes. The mixture was warmed up to room temperature and stirred for additional 2 hours. The reaction mixture was quenched with brine (200 mL), and partitioned between brine and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered, and concentrated to afford the title compound. MS (DCI/NH3) m/z 206 (M+H)+.

Workup

  1. temperaturecooled to 0° C
  2. temperatureThe mixture was warmed up to room temperature
  3. stirringstirred for additional 2 hours
  4. customThe reaction mixture was quenched with brine (200 mL)
  5. custompartitioned between brine and ethyl acetate
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-92cd4dae9d25463ea1c4983c2cb04440
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

Loading…