Aniline → HCID 13364167, compound

Participants

Reaction Steps

A solution of 2.9 g of potassium cyanide in 8 ml of water is added dropwise to a mixture of 16.3 g of 1-[4,4-bis(p-fluorophenyl)cyclohexyl]-4-piperidone (oil; its hydrochloride: m.p. 214°-217° C), 4.1 g of aniline and 40 ml of acetic acid at room temperature with stirring. The resulting mixture is stirred at room temperature for 6 hours and allowed to stand at room temperature overnight. The reaction mixture is poured into ice water, the aqueous mixture is made alkaline with potassium carbonate, and the alkaline mixture is extracted with chloroform. The extract is washed with water and dried over sodium sulfate, and the solvent is removed. The residual oil is dissolved in acetone, and 20% ethanolic hydrochloric acid is added thereto. After cooling the precipitated hydrochloride is collected by filtration and converted in a conventional manner into the base. The obtained crystals are recrystallized from a mixture of acetone and petroleum ether to give 1-[4,4-bis(p-fluorophenyl)cyclohexyl]-4-cyano-4-anilinopiperidine as white crystals, melting at 139° -140° C.

Provenance & Evidence