3-Phenylprop-2-En-1-Ol → N-Methyl-N-(3-phenylprop-2-en-1-yl)aniline

HRID 1627955Notes

Reaction equation

HRID 1627955 reaction equation
[CH2:1](O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].C(OC)=O>[Cl-].[Na+].O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:1]([N:12]([CH3:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 3083-Phenylprop-2-En-1-OlHCID 7515N-MethylanilineHCID 7865Methyl formateHCID 11430Potassium Carbonate

Product 1

HCID 53825062N-Methyl-N-(3-phenylprop-2-en-1-yl)anilineYield 92%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

Cinnamyl alcohol (100 mg, 0.75 mmol), N-methylaniline (53 mg, 0.50 mmol), dppf (14 mg, 0.025 mmol), K2CO3 (207 mg, 1.5 mmol) and [Pd(allyl)Cl]2 (4.5 mg, 0.0125 mmol) were sequentially added under argon to a reaction tube equipped with a stir bar and a septum. Degassed TPGS-M-PEG-750 solution (1.0 mL, 2 wt %), and HCO2Me (0.12 mL, 2.0 mmol) were added by syringe and vigorously stirred for 20 h. After the reaction, the contents of the flask were diluted with brine and extracted with EtOAc. The solution obtained was dried over anhydrous MgSO4, filtered, and concentrated by rotary evaporation. The residue was purified by flash chromatography eluting with 10% EtOAc/hexanes to afford the product as a pale yellow liquid (102 mg, 92%).

Workup

  1. customequipped with a stir bar
  2. customAfter the reaction
  3. extractionextracted with EtOAc
  4. customThe solution obtained
  5. dry with materialwas dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by flash chromatography
  9. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-002d83de58fa4af3832c5e34cfdce71e
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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