Iodine → 1-(1-Phenylcyclohexyl)-4-hydroxypiperidine

Participants

Reaction Steps

To bromobenzene (4.1 mL) and magnesium turnings (4 g) in 200 mL dry tetrahydrofuran under nitrogen was added a crystal of iodine and 10 drops of 1,2-dibromoethane. After small bubbles began to form, the reaction was stirred and heated to reflux for 4 hours. After cooling to room temperature 1-(1-cyanocyclohexyl)-4-hydroxypiperidine (2 g) was added. After 17 hours, the reaction was filtered, 120 mL saturated ammonium chloride was added and the mixture was extracted with ethyl ether. The ether layer was dried and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluted with the appropriate mixture of methanol and chloroform to yield pure 1-(1-Phenylcyclohexyl)-4-hydroxypiperidine.

Provenance & Evidence