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

HRID 2036417Notes

Reaction equation

HRID 2036417 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-d36aeb69211d4a45911ccbe3c55b5113
Source dataset
uspto-grants-2013_11
Patent number
US08575157B2

Reaction notes

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