Potassium Iodide → Hydrochloric Acid

Participants

Reaction Steps

To a suspension of 2 g. of trans 4-(p-fluorophenyl)cyclohexylamine hydrochloride (I) (prepared as in Example 20) in 30 ml. of dimethylformamide, 0.36 g. of 56% sodium hydride in mineral oil is added. Following about 25 minutes of stirring, there is added successively, 2.42 g. of potassium carbonate, 1.49 g. of potassium iodide and 2.18 g. of the 2,2-dimethyl-1,3-propanediol ketal of 4-chloro-4'-fluorobutyrophenone. The mixture is stirred in an oil bath at 90° for about 18 hours, allowed to cool and then dissolved in benzene and water. The organic layer is washed thoroughly with water and brine and then taken to dryness. The residue is dissolved in 80 ml. of methanol; 40 ml. of 2.5N hydrochloric acid is added, mixture stirred for about 1 hour and then concentrated under vacuum. The precipitated solid is collected on a filter. Two recrystallizations from methanol: 2.5N hydrochloric acid gives pure trans 4'-fluoro-4-{[ 4-(p-fluorophenyl)cyclohexyl]amine}butyrophenone hydrochloride (I), m.p. 193° to 197° C.

Provenance & Evidence