Hydrochloric Acid → 3-(Dimethylamino)-1-(3-fluorophenyl)propan-1-one

HRID 1191765Notes

Reaction equation

HRID 1191765 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:11][NH:12][CH3:13].Cl.[CH2:15](O)C>>[CH3:11][N:12]([CH3:15])[CH2:13][CH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[O:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 702EthanolHCID 99673-Fluoroacetophenone

Product 1

HCID 217067003-(Dimethylamino)-1-(3-fluorophenyl)propan-1-oneYield 88%

Procedure

1-(3-Fluorophenyl)ethanone (17 g, 0.123 mol), dimethylamine (13.7 g, 0.172 mol), and paraformaldephyde (5.5 g, 0.185 mol) were suspended in ethanol (50 mL), and conc HCl solution (0.3 mL) was added. The mixture was heated at reflux overnight. The solvent was removed under vacuum, and the residue was washed with EtOAc (3×) to give 3-(dimethylamino)-1-(3-fluorophenyl)propan-1-one (20.7 g, 88%), which was used for the next step without purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under vacuum
  4. washthe residue was washed with EtOAc (3×)

Sources & evidence

ORD record
ord-acfb2725a4ff49d49070f509ab58fdf8
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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