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| | alpha,alpha-Diphenyl-4-piperidinomethanol Basic information | | Preparation |
| | alpha,alpha-Diphenyl-4-piperidinomethanol Chemical Properties |
| 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) | | pka | 13.32±0.29(Predicted) | | form | Solid | | color | White to light beige | | InChI | InChI=1S/C18H21NO/c20-18(15-7-3-1-4-8-15,16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-10,17,19-20H,11-14H2 | | InChIKey | ZMISODWVFHHWNR-UHFFFAOYSA-N | | SMILES | C(O)(C1CCNCC1)(C1=CC=CC=C1)C1=CC=CC=C1 | | CAS DataBase Reference | 115-46-8(CAS DataBase Reference) | | NIST Chemistry Reference | Azacyclonol(115-46-8) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 24/25 | | WGK Germany | WGK 3 highly water endangering | | RTECS | TN0470000 | | HS Code | 29333999 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2 |
| | alpha,alpha-Diphenyl-4-piperidinomethanol Usage And Synthesis |
| Preparation | Using 4-piperidinic acid as a starting material, N-ethoxycarbonyl-4-piperidinic acid methyl ester was prepared by reacting it with ethyl chloroformate in a one-pot reaction involving esterification and amino protection. This methyl ester was then reacted with magnesium phenyl bromide to prepare N-ethoxycarbonyl-α,α-diphenyl-4-piperidinol, which was finally hydrolyzed with potassium hydroxide to obtain the target compound. This process utilizes inexpensive and readily available raw materials, has a short synthetic route, is simple to operate, and achieves an overall yield of 68.8%. | | 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 | | Uses | Anxiolytic;H1 antagonist | | Uses | 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 |
| | alpha,alpha-Diphenyl-4-piperidinomethanol Preparation Products And Raw materials |
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