| Identification | More | [Name]
alpha,alpha-Diphenyl-4-piperidinomethanol | [CAS]
115-46-8 | [Synonyms]
2,2-DIPHENYL-4-PIPERIDONOMETHANOL
4-(ALPHA,ALPHA DIPHENYL) PIPERIDINE METHANOL
A,A-DIPHENYL-4-PIPERIDINEMETHANOL
ALPHA-(4-PIPERIDYL)BENZHYDROL
ALPHA,ALPHA-DIPHENYL-4-PIPERIDINEMETHANOL
ALPHA,ALPHA-DIPHENYL-4-PIPERIDINOMETHANOL
AZACYCLONAL
AZACYCLONOL
DIPHENYL-4-PIPERIDINEMETHANOL
DIPHENYL-PIPERIDIN-4-YL-METHANOL
gamma-pipradol
TIMTEC-BB SBB003057
4-Piperidinemethanol, alpha,alpha-diphenyl-
alpha,alpha-diphenyl-4-piperidinemethano
Ataractan
Azacyklonol
Calmeran
Diphenyl(4-piperidinyl)methanol
Diphenyl-4-piperidylmethanol
Frenoton | [EINECS(EC#)]
204-092-5 | [Molecular Formula]
C18H21NO | [MDL Number]
MFCD00066980 | [Molecular Weight]
267.37 | [MOL File]
115-46-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light beige crystalline powder | [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 | [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) |
| Questions And Answer | Back Directory | [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%. |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H319 | [Precautionary statements ]
P264-P270-P280-P301+P312-P305+P351+P338-P337+P313 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
WGK 3 highly water endangering | [RTECS ]
TN0470000 | [REACH Registrations]
Active | [HS Code ]
29333999 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Description]
alpha,alpha-Diphenyl-4-piperidinomethanol(115-46-8) 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]
white to light beige crystalline powder | [Originator]
Frenquel,Merrell,US,1955 | [Uses]
Anxiolytic;H1 antagonist | [Uses]
α-(4-Piperidyl)benzhydrol is a key intermediate in the synthesis of Fexofenadine (F322490). | [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 | [storage]
Store at -20°C |
|
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