Benzyl Bromide → 2-Benzyl-2-(dimethylamino)-1-(4-fluorophenyl)butan-1-one

HRID 1780029Notes

Reaction equation

HRID 1780029 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH:9]([N:12]([CH3:14])[CH3:13])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:15])[C:9]([N:12]([CH3:13])[CH3:14])([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 19049509HCID 19049509, compound

Product 1

HCID 193605992-Benzyl-2-(dimethylamino)-1-(4-fluorophenyl)butan-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100 g (0.48 mol) of 1-(4-fluorophenyl)-2-dimethylamino-butan-1-one (crude product from A) are dissolved in 330 ml of acetonitrile. 98.1 g (0.57 mol) of benzyl bromide are slowly added dropwise, with stirring. After the mixture has been stirred at room temperature for 12 hours, the solvent is distilled off in vacuo. The residue is dissolved in 500 ml of water and the solution is heated to 55°-60°. 113 g of a 34% NaOH solution (0.96 mol) are added dropwise at this temperature and the mixture is subsequently stirred for 30 minutes.

Workup

  1. stirringAfter the mixture has been stirred at room temperature for 12 hours
  2. distillationthe solvent is distilled off in vacuo
  3. dissolutionThe residue is dissolved in 500 ml of water
  4. temperaturethe solution is heated to 55°-60°
  5. stirringthe mixture is subsequently stirred for 30 minutes

Sources & evidence

ORD record
ord-9c0ca77228134c2e9e1936a6b51165b1
Source dataset
uspto-grants-1997_05
Patent number
US05629356

Reaction notes

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