P-Dimethylaminopropiophenone hydrochloride

PP-Dimethylacrylic acid, 460 Dimethylamine hydrochloride, 414, 416 Dimethylaminomethylindole, 1012,1013 P-Dimethylaminopropiophenone hydrochloride, 910, 911... 

About 600 g of p-dimethylaminopropiophenone hydrochloride were converted to the corresponding free base by the action of 1.5 N aqueous sodium hydroxide. Free base was dissolved in 2 L of THF, and the resulting solution added in dropwise fashion to a solution of 4 moles of diborane in 4 L of THF. The reaction mixture was stirred overnight. An additional mole of diborane in... 

P-Dimethylaminopropiophenone hydrochloride Hydrogen chloride 4-Trifluoromethylphenol Cyanogen bromide... 

P-Dimethylaminopropiophenone hydrochloride. Place 26 5 g. of dry dimethylamine hydrochloride, 10 g. of powdered paraformaldehyde and 30 g. (29-3 ml.) of acetophenone (Section IV,136) in a 250 ml. round-bottomed flask attached to a reflux condenser. Introduce 40 ml. of 95 per cent, ethanol to which 0-5 ml. of concentrated hydrochloric acid has been added, and reflux the mixture on a water bath for 2 hours the reaction mixture should ultimately be almost clear and homogeneous. Filter the yellowish solution (if necessary) through a hot water funnel ... 

To a mixture of 21.4g (0.1 mol) of dimethylaminopropiophenone hydrochloride and 13.0g (0.2 mol) of potassium cyanide in a 500-ml flask, add 260 ml of boiling water heat the heterogeneous mixture under reflux for 30 minutes. Part of the dimethylamine, which is eliminated in the reaction, distils collect this in dilute hydrochloric acid. Cool the reaction mixture in ice the oil solidifies and crystals form in the aqueous layer. Collect the solid [crude 3-benzoylpropionitrile, 10.5 g (66%)] by suction filtration and recrystallise it from benzene-light petroleum (b.p. 40-60 °C) the product separates as almost colourless blades, m.p. 76 °C. 

Conversion to phenyl vinyl ketone. Place an intimate mixture of 21.4 g (0.1 mol) of //-dimethylaminopropiophenone hydrochloride and 0.2 g of hydroquinone in a 100-ml round-bottomed flask. Attach a Claisen still-head fitted with a stout capillary air leak and condenser arranged for distillation under reduced pressure place a few crystals of hydroquinone in the receiving flask. Pyrolyse the amine hydrochloride by heating the flask in an electric mantle at 2 mmHg (oil immersion pump), and collect the crude ketone which distils between 70 and 90 °C. On redistillation 7g (51%) of pure phenyl vinyl ketone, b.p. 72-73 °C/3 mmHg (115 °C/18 mmHg), are obtained. Characterise... 

The Grignard solution (prepared from 53 g bromtoluene and 7.2 g magnesium in 300 ml of ether) was added dropwise to a solution of 35 g p-dimethylaminopropiophenone in 50 ml ether. The mixture was refluxed for 3 hours. Then the liquid phase was added to 500 parts of ice and 100 parts concentrated hydrochloric acid. l-Phenyl-l-p-tolyl-3-dimethylaminopropanol-l was crystallized. M.P. of hydrochloride of l-phenyl-l-p-tolyl-3-dimethylaminopropanol-1 185°C. 

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