Dimethylamine → HCID 19049509, compound

HRID 1780028Notes

Reaction equation

HRID 1780028 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 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 product 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 product
  6. customis used without further purification for the subsequent reaction

Sources & evidence

ORD record
ord-e374c2a4e834473a8f5f1728ba6fd8af
Source dataset
uspto-grants-1997_05
Patent number
US05629356

Reaction notes

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