Basic information Safety Supplier Related

phenoperidine

Basic information Safety Supplier Related

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
Mol File:
562-26-5.mol
More
Less

phenoperidine Chemical Properties

Boiling point:
508.8±50.0 °C(Predicted)
Density 
1.122±0.06 g/cm3(Predicted)
pka
14.31±0.20(Predicted)
More
Less

Safety Information

RIDADR 
3249
HazardClass 
6.1(b)
PackingGroup 
III
DEA Controlled Substances
CSCN: 9641
CSA SCH: Schedule I
NARC: Yes
More
Less

phenoperidine Usage And Synthesis

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

phenoperidineSupplier