BENZETIMIDE Chemical Properties

Melting point:

181-183°

alpha 

D20 +125° (chloroform)

Boiling point:

543.9±50.0 °C(Predicted)

Density 

1.178±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMSO: ≥ 100 mg/mL (275.89 mM)

pka

11.20±0.40(Predicted)

form 

Solid

color 

White to off-white

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

BENZETIMIDE Usage And Synthesis

Originator

Tremblex,Brocades,Italy,1981

Uses

Anticholinergic.

Definition

ChEBI: Dexetimide is a member of piperidines.

Manufacturing Process

400 parts glacial acetic acid are cooled to 10°C to 20°C. Then there are added first dropwise 300 parts concentrated sulfuric acid followed by portionwise addition of 50 parts dl-1-benzyl-4-(1,3-dicyano-1-phenylpropyl)-piperidine hydrochloride at the same temperature. After the addition is complete, the whole is heated to 125°C in the course of 15 to 20 minutes. This temperature is then maintained for 10 minutes. After cooling, the reaction mixture is poured into ice, alkalized with NH4OH at a temperature < 20°C and extracted with chloroform. The chloroform layer is first washed twice with a K2CO3 5% solution, and then washed twice with water, dried over MgSO4, filtered and evaporated. The residue is dissolved in a mixture of 320 parts acetone and 600 parts diisopropylether, filtered and HCl gas is introduced into the filtrate. The solid hydrochloride is filtered off and dried, to yield 43 parts less pure lbenzyl-4-(2.6-dioxo-3-phenyl-3-piperidyl)-piperidine hydrochloride, melting point 283°C to 294°C.
A sample of 4 parts is recrystallized from a boiling mixture of 80 parts isopropanol, 40 parts methanol and 500 parts water. The whole is filtered and after cooling the filtrate overnight at -20°C, 1-benzyl-4-(2,6-dioxo-3phenyl-3- piperidyl)-piperidine hydrochloride is obtained, melting point 299°C to 301.5°C, as a white amorphous powder.
The dextro-isomer may be separated via the dextro-camphorsulfonate of the base.

Therapeutic Function

Anticholinergic (ophthalmic)

BENZETIMIDE(21888-98-2)Related Product Information

• (1-Methyl-piperidin-4-yl)-acetaldehyde
• 7-DIETHYLAMINOHEPTYLAMINE
• BENZETIMIDE HCL,BENZETIMIDE HYDROCHLORIDE
• 1,5-DIAMINO-2-METHYLPENTANE
• 4-Benzylpiperidine
• DL-Glutethimide
• 2-PHENYLBUTYRAMIDE
• 2,2-DI-N-PROPYLACETAMIDE
• 3,3-DIMETHYLPIPERIDINE
• 4-BUTYLPIPERIDINE
• 2-Piperidone
• 4-N-PROPYLPIPERIDINE
• BENZETIMIDE
• alpha-Methylhydratropamide
• N-(2-PIPERIDIN-4-YL-ETHYL)-ACETAMIDE
• (R)-2-PHENYLPROPYLAMIDE
• 4-tert-butylpiperidine
• 3-methyl-3-phenylpiperidine