Hydrochloric Acid → 3-(Dimethylamino)-1-(2-fluorophenyl)propan-1-one

HRID 2037521Notes

Reaction equation

HRID 2037521 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[CH3:11][NH:12][CH3:13].[CH2:14]=O.Cl>C(O)C>[CH3:11][N:12]([CH3:14])[CH2:13][CH2:9][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 96744o-Fluoroacetophenone

Product 1

HCID 581091723-(Dimethylamino)-1-(2-fluorophenyl)propan-1-oneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Fluorophenyl)ethanone (170 g, 1.23 mol), dimethylamine (137 g, 1.72 mol), and paraformaldehyde (55 g, 1.85 mol) were suspended in ethanol (500 mL), then concentrated HCl (3 mL) was added, and the mixture was heated to reflux overnight. The solvent was removed under vacuum. The residue was washed with EtOAc for 3 times to give 3-(dimethylamino)-1-(2-fluorophenyl)propan-1-one (207 g, 88%), which was used for the next step without purification. 1H NMR (CDCl3): δ=2.69 (s, 6H), 2.52 (m, 4H), 7.30 (m, 2H), 7.66 (m, 1H), 7.96 (m, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed under vacuum
  4. washThe residue was washed with EtOAc for 3 times

Sources & evidence

ORD record
ord-d5178b2c42624f028af0c2a721689dcd
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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