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phenoperidine

phenoperidine
phenoperidine structure
CAS No.
562-26-5
Chemical Name:
phenoperidine
Synonyms
phenoperidine;IPOPQVVNCFQFRK-UHFFFAOYSA-N;ethyl 1-(3-hydroxy-3-phenylpropyl)-4-phenylpiperidine-4-carboxylate;1-(3-Hydroxy-3-phenylpropyl)-4-phenylpiperidine-4-carboxylic acid ethyl ester;4-Piperidinecarboxylic acid, 1-(3-hydroxy-3-phenylpropyl)-4-phenyl-, ethyl ester
CBNumber:
CB7930605
Molecular Formula:
C23H29NO3
Formula Weight:
367.48
MOL File:
562-26-5.mol

phenoperidine Properties

Boiling point:
508.8±50.0 °C(Predicted)
Density 
1.122±0.06 g/cm3(Predicted)
pka
14.31±0.20(Predicted)
FDA UNII
G9BH09J4JW
SAFETY
  • Risk and Safety Statements
RIDADR  3249
HazardClass  6.1(b)
PackingGroup  III

phenoperidine Chemical Properties,Uses,Production

Originator

Operidine ,Janssen ,US ,1965

Manufacturing Process

The 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 Function

Analgesic

phenoperidine Preparation Products And Raw materials

Raw materials

Preparation Products

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