Benzyl Bromide → 2-(Dimethylamino)-1-(4-fluorophenyl)-2-methyl-3-phenylpropan-1-one

HRID 376958Notes

Reaction equation

HRID 376958 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH:9]([N:11]([CH3:13])[CH3:12])[CH3:10])=[CH:4][CH:3]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(N(C)C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:14])[C:9]([N:11]([CH3:13])[CH3:12])([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 18755062HCID 18755062, compound

Product 1

HCID 187550662-(Dimethylamino)-1-(4-fluorophenyl)-2-methyl-3-phenylpropan-1-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
105 °C

Procedure

11.2 g of sodium hydride (66%) are washed with hexane to remove oil, and added to 200 ml of dry dimethylacetamide. 50.0 g (0.256 mol) of 1-(4-fluorophenyl)-2-dimethylamino-propan-1-one (prepared by the method described in U.S. Pat. No. 5,534,629) are dissolved in 50 ml of dry dimethylacetamide and added dropwise to the above described solution. Successively, 48.2 g (0.282 mol) of benzyl bromide are slowly added dropwise with stirring and warmed up to 105° C. When the mixture has been stirred at this temperature for 12 h, the reaction mixture is poured to 500 ml of ice/water and extracted with toluene. The organic phase is washed with water, dried over MgSO4 and evaporated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:20) as eluent. The structure is confirmed by the 1H-NMR-spectrum, measured in CDCl3. The signals (δ in ppm) are 1.17 (s,3H), 2.33 (s,6H), 2.96 (d, 1H), 3.39 (d, 1H), 6.87 (m,2H), 7.03-7.13 (m,5H), 8.55 (m, 2H).

Workup

  1. wash11.2 g of sodium hydride (66%) are washed with hexane
  2. customto remove oil
  3. additionadded to 200 ml of dry dimethylacetamide
  4. additionadded dropwise to the
  5. stirringWhen the mixture has been stirred at this temperature for 12 h
  6. extractionextracted with toluene
  7. washThe organic phase is washed with water
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:20) as eluent

Sources & evidence

ORD record
ord-35034db53b474c67bdd120ba4ef02c45
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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