3,5-Dimethoxyphenol → Phenoxy propargyl amine

HRID 1264364Notes

Reaction equation

HRID 1264364 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C([O-])([O-])=O.[K+].[K+].C[O:12][C:13]1[CH:14]=[C:15](O)[CH:16]=[C:17](OC)[CH:18]=1.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[O:12]([NH:4][CH2:1][C:2]#[CH:3])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 103833,5-DimethoxyphenolHCID 11430Potassium CarbonateHCID 239041PropargylamineHCID 21226206Ethyl acetate hexane

Product 1

HCID 22485267Phenoxy propargyl amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of the propargyl amine of Part B. Example 38 (2 g, 5.6 mmol) and powdered K2CO3 (1.9 g, 13.7 mmol) in N,N-dimethylformamide (20 mL) was added 3,5-dimethoxyphenol (2.18 g, 13.7 mmol) at ambient temperature. The resulting composition was heated to 90 degrees Celsius for 36 hours. The solution was concentrated under high vacuum and the residue was dissolved in ethyl acetate. The organic layer was washed with 1N NaOH, H2O and dried over MgSO4. Chromatography (on silica, ethyl acetate/hexane) provided phenoxy propargyl amine as light yellow gel (2.76 g, quantitative yield).

Workup

  1. customat ambient temperature
  2. temperatureThe resulting composition was heated to 90 degrees Celsius for 36 hours
  3. concentrationThe solution was concentrated under high vacuum
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic layer was washed with 1N NaOH, H2O
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-a16644e8e8db45d9806b57512cd91ab3
Source dataset
uspto-grants-2003_04
Patent number
US06541489B1

Reaction notes

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