| Identification | Back Directory | [Name]
phenoperidine | [CAS]
562-26-5 | [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 | [EINECS(EC#)]
209-229-2 | [Molecular Formula]
C23H29NO3 | [MOL File]
562-26-5.mol | [Molecular Weight]
367.48 |
| Safety Data | Back Directory | [RIDADR ]
3249 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [DEA Controlled Substances]
CSCN: 9641
CSA SCH: Schedule I
NARC: Yes |
| Hazard Information | Back Directory | [Originator]
Operidine ,Janssen ,US ,1965 | [Definition]
ChEBI: Phenoperidine is a member of piperidines. | [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 |
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