phenoperidine

phenoperidine Basic information
Product Name:phenoperidine
Synonyms:phenoperidine;1-(3-Hydroxy-3-phenylpropyl)-4-phenylpiperidine-4-carboxylic acid ethyl ester;IPOPQVVNCFQFRK-UHFFFAOYSA-N;ethyl 1-(3-hydroxy-3-phenylpropyl)-4-phenylpiperidine-4-carboxylate;4-Piperidinecarboxylic acid, 1-(3-hydroxy-3-phenylpropyl)-4-phenyl-, ethyl ester
CAS:562-26-5
MF:C23H29NO3
MW:367.48
EINECS:209-229-2
Product Categories:
Mol File:562-26-5.mol
phenoperidine Structure
phenoperidine Chemical Properties
Boiling point 508.8±50.0 °C(Predicted)
density 1.122±0.06 g/cm3(Predicted)
pka14.31±0.20(Predicted)
Safety Information
RIDADR 3249
HazardClass 6.1(b)
PackingGroup III
MSDS Information
phenoperidine Usage And Synthesis
OriginatorOperidine ,Janssen ,US ,1965
Manufacturing ProcessThe starting materials for the overall process are phenylacetonitrile with bischloroethyl toluene sulfonyl amide. These react to give a product which hydrolyzes to normeperidine (4-carboethoxy-4-phenylpiperidine). Condensation of that material with benzoylethylene gives the ketone: β-(4carboethoxy-4-phenylpiperidino)propiophenone.
A reaction mixture was prepared containing 4 grams of β-(4-carboethoxy-4phenylpiperidino)-propiophenone hydrochloride, 100 ml of methanol and about 0.5 gram of platinum oxide catalyst. The mixture was placed in a low pressure hydrogenation apparatus and was hydrogenated at a temperature of about 27°C and a pressure of about 3.5 atmospheres of hydrogen to convert the keto group of the β-(4-carboethoxy-4-phenylpiperidino)-propiophenone to a hydroxy group, and to form 3-(4-carboethoxy-4-phenylpiperidino)-1-phenyl-1propanol hydrochloride. After the hydrogenation was complete, the catalyst was separated from the reaction mixture by filtration, and the filtrate was evaporated to dryness in vacuo leaving a residue containing 3-(4carboethoxy-4-phenylpiperidino)-1-phenyl-l-propanol hydrochloride. The residue was digested with ethyl acetate thereby causing 3-(4-carboethoxy-4phenylpiperidino)-1-phenyl-1-propanol hydrochloride to crystallize. This compound melted at about 188°-189°C after being recrystallized three times from an ethyl acetate-methanol solvent mixture, according to US Patent 2,951,080.
Therapeutic FunctionAnalgesic
phenoperidine Preparation Products And Raw materials
Raw materialsHydrogen-->Benzeneacetonitrile
Tag:phenoperidine(562-26-5) Related Product Information
Alverine CHEMBRDG-BB 4015185 4-Methylisonipecotic acid ethyl ester ETHYL 1,4-DIMETHYLPIPERIDINE-4-CARBOXYLATE 1,4-DIMETHYLPIPERIDINE-4-CARBOXYLIC ACID PETHIDINIC ACID MEPERIDINE NORMEPERIDINE phenoperidine