Hydrochloric Acid → 3-(Dimethylamino)-1-(4-fluorophenyl)propan-1-one hydrochloride

HRID 491566Notes

Reaction equation

HRID 491566 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11]=O.[ClH:13].[CH3:14][NH:15][CH3:16].Cl>CC(O)C>[ClH:13].[CH3:14][N:15]([CH3:11])[CH2:16][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 98284'-FluoroacetophenoneHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 123227913-(Dimethylamino)-1-(4-fluorophenyl)propan-1-one hydrochlorideYield 94.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4′-fluoroacetophenone (5 g, 36.2 mmol) in propan-2-ol (90 ml) was added paraformaldehyde (4.35 g, 0.145 mol), dimethylamine hydrochloride (54.2 mmol) and concentrated HCl (0.8 ml). The reaction was heated at reflux for 18 h and on cooling the solvent was removed in vacuo. The residue was treated with acetone giving a white precipitate which was collected by filtration and dried in vacuo to give the title compound as a white solid (7.9 g). MS (ES): MH+ 196.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 h
  3. temperatureon cooling the solvent
  4. customwas removed in vacuo
  5. additionThe residue was treated with acetone giving a white precipitate which
  6. filtrationwas collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c44a2278571441c6834426650a6141d8
Source dataset
uspto-grants-2009_05
Patent number
US07531558B2

Reaction notes

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