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HomeProduct name listalpha,alpha-Diphenyl-4-piperidinomethanol

alpha,alpha-Diphenyl-4-piperidinomethanol

Synonym(s):Azacyclonol;Diphenyl-4-piperidinemethanol

  • CAS NO.:115-46-8
  • Empirical Formula: C18H21NO
  • Molecular Weight: 267.37
  • MDL number: MFCD00066980
  • EINECS: 204-092-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2025-01-27 09:38:02
alpha,alpha-Diphenyl-4-piperidinomethanol Structural

What is 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

Properties of alpha,alpha-Diphenyl-4-piperidinomethanol

Melting point: 160-163 °C
Boiling point: 410.55°C (rough estimate)
Density  1.0449 (rough estimate)
vapor pressure  0Pa at 25℃
refractive index  1.5100 (estimate)
storage temp.  Store below +30°C.
solubility  Chloroform, Methanol (Slightly, Sonicated)
form  Solid
pka 13.32±0.29(Predicted)
color  White to light beige
CAS DataBase Reference 115-46-8(CAS DataBase Reference)
NIST Chemistry Reference Azacyclonol(115-46-8)

Safety information for alpha,alpha-Diphenyl-4-piperidinomethanol

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for alpha,alpha-Diphenyl-4-piperidinomethanol

InChIKey ZMISODWVFHHWNR-UHFFFAOYSA-N

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