ChemicalBook > CAS DataBase List > bezitramide

bezitramide

Product Name
bezitramide
CAS No.
15301-48-1
Chemical Name
bezitramide
Synonyms
R 4845;bezitramide;FLKWNFFCSSJANB-UHFFFAOYSA-N;1-[1-(3-Cyano-3,3-diphenylpropyl)-4-piperidinyl]-1,3-dihydro-3-(1-oxopropyl)-2H-benzimidazol-2-one;1-Piperidinebutanenitrile, 4-[2,3-dihydro-2-oxo-3-(1-oxopropyl)-1H-benzimidazol-1-yl]-α,α-diphenyl-
CBNumber
CB5901881
Molecular Formula
C31H32N4O2
Formula Weight
492.61
MOL File
15301-48-1.mol
More
Less

bezitramide Property

Melting point:
145-149°; mp 124.5-126°
Boiling point:
586.35°C (rough estimate)
Density 
1.1470 (rough estimate)
refractive index 
1.6000 (estimate)
pka
8.21±0.10(Predicted)
color 
White, crystalline powder
More
Less

Safety

Toxicity
LD50 orally in mice, rats: 2101, 141 mg/kg (Janssen)
More
Less

Hazard and Precautionary Statements (GHS)

More
Less

bezitramide Chemical Properties,Usage,Production

Originator

Bezitramide,ZYF Pharm Chemical

Uses

Bezitramide is a narcotic analgesic agonist with modified pipiridine N-substituents whose binding affinity to the ORL1 and N-methyl-D-aspartate (NMDA) receptors is of research interest.

Definition

ChEBI: Bezitramide is a nitrile.

Manufacturing Process

A mixture of 6.9 parts 4-bromo-2,2-diphenylbutyronitrile, 5 parts 4-(2-oxo-1- benzimidazolinyl)piperidine, 7.3 parts sodium carbonate, a few crystals of potassium iodide in 160 parts 4-methyl-2-pentanone is stirred and refluxed for 12 hours. After cooling the reaction mixture, 100 parts water is added. The aqueous layer is separated and extracted with 4-methyl-2-pentanone. The combined organic layer are dried over MgSO4 and evaporated. The oily residue is dissolved in a mixture of 24 parts diisopropylether and 24 parts isopropanol. After cooling overnight to -20°C, 5.3 parts product are obtained. This crop is boiled in 72 parts 4-methyl-2-pentanone and cooled to 0°C, yielding 1-(3-cyano-3,3-diphenylpropyl)-4-(2-oxo-1-benzimidazolinyl) piperidine, melting point 225-226°C, as a grey-white amorphous powder.
A mixture of 5 parts 1-(3-cyano-3,3-diphenylpropyl)-4-(2-oxo-1- benzimidazolinyl)piperidine, 7.5 parts propionic acid anhydride and 80 parts benzene is stirred and refluxed for 16 hours. After cooling, the reaction mixture is washed twice with 100 parts water. The aqueous layer is dried over potassium carbonate, filtered and evaporated. The residue is recrystallized from 60 parts of ether, yielding 4 parts crude 1-(3-cyano-3,3-diphenylpropyl)- 4-(2-oxo-3-propionyl-1-benzimidazolinyl)piperidine. This crop is recrystallized from 20 parts m-methyl-2-pentanone 4-ethyl-2-pentanone, yielding 1-(3-cyano-3,3-diphenylpropyl)-4-(2-oxo-3-propionyl-1-benzimidazolinyl)piperidine with melting point: 124.5-126°C as a pale yellow amorphous powder.

Therapeutic Function

Narcotic analgesic, Antitussive

Safety Profile

Poison by ingestion. Caution: Maybe habit forming. This is a controlled substance (opiate)listed in the U.S. Code of Federal Regulations, Title 21Part 1308.12 (1985). When heated to decomposition itemits toxic fumes of NOx and CN-.

bezitramide Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

bezitramide Suppliers

15301-48-1, bezitramideRelated Search:


  • bezitramide
  • 1-[1-(3-Cyano-3,3-diphenylpropyl)-4-piperidinyl]-1,3-dihydro-3-(1-oxopropyl)-2H-benzimidazol-2-one
  • R 4845
  • FLKWNFFCSSJANB-UHFFFAOYSA-N
  • 1-Piperidinebutanenitrile, 4-[2,3-dihydro-2-oxo-3-(1-oxopropyl)-1H-benzimidazol-1-yl]-α,α-diphenyl-
  • 15301-48-1