Dimethylamine → HCID 19049509, compound

HRID 1734745Notes

Reaction equation

HRID 1734745 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH:9](Br)[CH2:10][CH3:11])=[CH:4][CH:3]=1.FCCCC(C1C=CC=CC=1)=O.[CH3:26][NH:27][CH3:28]>C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH:9]([N:27]([CH3:28])[CH3:26])[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 18354700HCID 18354700, compoundHCID 190494002-Bromo-1-(4-fluorophenyl)butan-1-one

Product 1

HCID 19049509HCID 19049509, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

240 g (0.98 mol) of 1-(4-fluorophenyl)-2-bromobutan-1-one (prepared by bromination of 4-fluorobutyrophenone by the method described in EP-A-3,002) are dissolved in 250 ml of diethyl ether. This solution is slowly added dropwise to a mixture of 265 g (5.87 mol) of the dimethylamine in 1250 ml of diethyl ether at 0°. After the mixture has been stirred at 0° for 12 hours, the excess dimethylamine is removed at room temperature by blowing through N2 and the suspension is poured onto water. The ether phase is washed with water and dried over MgSO4. After filtration and evaporation of the solution, 202.8 g of crude produce remain as a colourless oil, which is used without further purification for the subsequent reaction.

Workup

  1. customthe excess dimethylamine is removed at room temperature
  2. additionthe suspension is poured onto water
  3. washThe ether phase is washed with water
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and evaporation of the solution, 202.8 g of crude
  6. customproduce
  7. customis used without further purification for the subsequent reaction

Sources & evidence

ORD record
ord-a94cbe19cecd450fb4820c99764eadec
Source dataset
uspto-grants-1996_07
Patent number
US05534629

Reaction notes

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