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

HRID 267828Notes

Reaction equation

HRID 267828 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 three 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-2methylpropiophenone

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-d40289b0266744d6903eea13a414e190
Source dataset
uspto-grants-1976_03
Patent number
US03944600

Reaction notes

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