alpha,alpha-Diphenyl-4-piperidinomethanol

Description

alpha,alpha-Diphenyl-4-piperidinomethanol is an important organic synthetic substance for the synthesis of diphenyl-4-piperidinomethanol. It is also used as a pharmaceutical intermediate in the preparation of terfenadine and Fexofenadine hydrochloride.

Chemical properties

α,α-Diphenyl-4-piperidinemethanol has the appearance of a white to almost white powder to crystals with a melting point of 163 °C. Store at -20 °C.

Originator

Frenquel,Merrell,US,1955

The Uses of alpha,alpha-Diphenyl-4-piperidinomethanol

Anxiolytic;H1 antagonist

The Uses of alpha,alpha-Diphenyl-4-piperidinomethanol

α-(4-Piperidyl)benzhydrol is a key intermediate in the synthesis of Fexofenadine (F322490). Fexofenadine EP Impurity E.

Definition

ChEBI: Diphenyl(4-piperidinyl)methanol is a diarylmethane.

Manufacturing Process

A mixture of 26 g (0.1 mol) of α-(4-pyridyl)-benzhydrol, 1.5 g of platinum oxide, and 250 ml of glacial acetic acid is shaken at 50-60°C under hydrogen at a pressure of 40-50 lb/in2. The hydrogenation is complete in 2 to 3 hours. The solution is filtered and the filtrate evaprated under reduced pressure. The residue is dissolved in a mixture of equal parts of methanol and butanone and 0.1 mol of concentrated hydrochloric acid is added. The mixture is cooled and filtered to give about 30 g of α-(4-piperidyl)benzhydrol hydrochloride, MP 283- 285°C, as a white, crystalline substance.
The free base is readily obtained from the hydrochloride salt by treatment with ammonia and when so obtained has a melting point of 160-161°C.

brand name

Frenquel (Marion Merrell Dow).

Therapeutic Function

Tranquilizer