Hydrochloric Acid → 1-(3-((Dimethylamino)methyl)-4-methoxyphenyl)ethanone

HRID 30607Notes

Reaction equation

HRID 30607 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[CH2:7][N:8]([CH3:10])[CH3:9].[CH2:14]([O:18]C=C)[CH2:15]CC.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:9][N:8]([CH2:7][C:6]1[CH:11]=[C:2]([C:14](=[O:18])[CH3:15])[CH:3]=[CH:4][C:5]=1[O:12][CH3:13])[CH3:10]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 8818661-(5-Bromo-2-methoxyphenyl)-N,N-dimethylmethanamine

Product 1

HCID 8170251-(3-((Dimethylamino)methyl)-4-methoxyphenyl)ethanoneYield 42%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(5-Bromo-2-methoxy-benzyl)-dimethyl-amine (29 mmol), Butoxy-ethene (100 mmol), Palladium acetate (0.9 mmol), 1,3-Bis(diphenylphosphino)propane (1.8 mmol), and potassium carbonate were suspended in DMF (50 ml) and H2O under argon. Heated at 80° C. overnight. Poured into hydrochloric acid (2 M) and stirred for 1 hour. The mixture was adjusted to basic pH and extracted with CH2Cl2. The organic phase was evaporated on celite and the residue was purified by flash chromatography to give the title product as orange oil in 42% yield. 1H-NMR (CDCl3) δ 7.90 (s, 1H), 7.88 (dd, 1H), 6.89 (d, 1H), 3.88 (s, 3H), 3.44 (s, 2H), 2.55 (s, 3H), 2.25 (s, 6H).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic phase was evaporated on celite
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a917ce6dcd2d4fe08b04825b251cbac2
Source dataset
uspto-grants-2008_09
Patent number
US07423181B2

Reaction notes

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