Formaldehyde → 3-(Dimethylamino)-1-(4-fluorophenyl)-2-methylpropan-1-one

HRID 918291Notes

Reaction equation

HRID 918291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.Cl.[CH3:13][NH:14][CH3:15].[CH2:16]=O>>[CH3:13][N:14]([CH3:15])[CH2:10][CH:9]([CH3:16])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:11]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 680044-Fluoropropiophenone

Product 1

HCID 215218873-(Dimethylamino)-1-(4-fluorophenyl)-2-methylpropan-1-one

Procedure

A mixture of 15.2 g. (0.10 mole) of 4'-fluoropropiophenone, 8.2 g. (0.10 mole) of dimethylamine hydrochloride, 3.6 g. (0.12 mole) of paraformaldehyde in 20 ml. of absolute alcohol was stirred at 95°-100°C for 3 hours. The mixture is cooled and the precipitated product is filtered. The product is dissolved in water, made alkaline with sodium hydroxide. The free base is extracted into ether. The ether layer is dried over anhydrous sodium sulfate and concentrated in vacuo to give 3-dimethylamino-4'-fluoro-2-methylpropiophenone.

Workup

  1. additionA mixture of 15.2 g
  2. temperatureThe mixture is cooled
  3. filtrationthe precipitated product is filtered
  4. dissolutionThe product is dissolved in water
  5. extractionThe free base is extracted into ether
  6. dry with materialThe ether layer is dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78a6d675e8f04bb88e494164774cc8da
Source dataset
uspto-grants-1976_07
Patent number
US03970693

Reaction notes

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