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Anileridine

Anileridine
Anileridine structure
CAS No.
144-14-9
Chemical Name:
Anileridine
Synonyms
Adopol;Apidol;Alidine;Adopol-d4;Ethyl 1-(4;anileridine base;LKYQLAWMNBFNJT-UHFFFAOYSA-N;1-(p-AMinophenethyl)-4-phenylisonipecotic Acid Ethyl Ester;1-(p-AMinophenethyl)-4-phenylisonipecotic Acid-d4 Ethyl Ester;1-(p-AMinophenethyl)-4-phenylpiperidine-4-carboxylic Acid Ethyl Ester
CBNumber:
CB81178032
Molecular Formula:
C22H28N2O2
Formula Weight:
352.47
MOL File:
144-14-9.mol

Anileridine Properties

Melting point:
83°C
Boiling point:
486.07°C (rough estimate)
Density 
1.1096 (rough estimate)
refractive index 
1.6500 (estimate)
pka
8.41±0.10(Predicted)
form 
Solid
SAFETY
  • Risk and Safety Statements
RIDADR  1544
HazardClass  6.1(b)
PackingGroup  III
Toxicity LD50 orl-rat: 175 mg/kg 27ZIAQ -,-,65

Anileridine Chemical Properties,Uses,Production

Originator

Leritine HCl,Merck Sharp and Dohme,US,1958

Uses

A synthetic analgesic drug. 4-phenylpiperidine derivative that is an analog of Meperidine (M223900) with increased analgesic activity.

Definition

ChEBI: A piperidinecarboxylate ester that is the ethyl ester of isonipecotic acid in which the hydrogen alpha- to the carboxyl group is substituted by a phenyl group, and the hydrogen attached to the nitrogen is substituted by a 2-(4-aminophenyl) thyl group.

Manufacturing Process

A mixture of 7.8 grams (0.05 mol) of β-(p-aminophenyl)ethyl chloride hydrochloride, 12.5 grams (0.025 mol) of 4-phenyl-4-carboethoxypiperidine carbonate, 10.5 grams (0.125 mol) sodium bicarbonate, and 100 cc of anhydrous ethanol are mixed, stirred and heated under reflux for a period of approximately 40 hours and then concentrated in vacuum to dryness. The residual material is triturated with 50 cc of water, decanted, washed by decantation with an additional 50 cc of water, and then dried in vacuum to give N-[β-(p-aminophenyl)ethyl]-4-phenyl-4-carboethoxypiperidine.
The N-[β-(p-aminophenyl)ethyl]-4-phenyl-4-carboethoxypiperidine is dissolved in 50 cc of hot anhydrous ethanol, an excess (about 20 cc) of 20% alcoholic hydrochloric acid solution is added; upon scratching the side of the container crystals form. One hundred cubic centimeters of ether are then added to the mixture, the ethereal mixture is cooled, and the crystalline material which precipitates is recovered by filtration, washed with ether, and dried to give 12.7 grams of N-[β-(p-aminophenyl)ethyl]-4-phenyl-4-carboethoxypiperidine dihydrochloride which can be further purified by recrystallization from ethanol or methanal to give substantially pure material; MP 275-277°C.

brand name

Leritine (Merck).

Therapeutic Function

Narcotic analgesic

Safety Profile

Poison by ingestion,subcutaneous, intravenous, and intraperitoneal routes.When heated to decomposition it emits toxic fumes ofNOx.

Anileridine Preparation Products And Raw materials

Raw materials

Preparation Products

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