156366-27-7

Basic information

• Product Name: N-tritylamlodipine
• Synonyms: N-tritylamlodipine
• CAS NO: 156366-27-7
• Molecular Weight: 651.202
• Mol File: 156366-27-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-tritylamlodipine(CAS DataBase Reference)
• NIST Chemistry Reference: N-tritylamlodipine(156366-27-7)
• EPA Substance Registry System: N-tritylamlodipine(156366-27-7)

Safety Data

• Hazardous Substances Data: 156366-27-7(Hazardous Substances Data)

Upstream product

• 156366-26-6 ethyl 4-(2'-(N-tritylamino)ethoxy)acetoacetate 
• 89-98-5 2-chloro-benzaldehyde 
• 14205-39-1 methyl (E)-3-aminocrotonate 
• 957939-15-0 E/Z-ethyl 2-(2-chlorobenzylidene)-4-(2-tritylaminoethoxy)acetoacetate 
• 14205-39-1 methyl 3-aminocrotonate 

Downstream Products

• 111470-99-6 amlodipine besylate 
• 331258-31-2 diethyl 2,6-bis[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate 
• 140171-66-0 dimethyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate 

Relevant articles and documents

Amlodipine benzenesulfonate: A mechanistic investigation of its industrial preparation via detritylation of N-tritylamlodipine and related NMR studies

Kinetics and product analysis of detritylation of N-tritylamlodipine by benzenesulfonic acid in methanol, methanol-chloroform (volume ratio 9:1), ethanol, 2-propanol, and methanol/2-propanol (mole ratio 1:1) have been investigated by HPLC; amongst these reaction conditions are ones closely similar to those of one method of manufacturing amlodipine benzenesulfonate. Kinetics of detritylation of Ntritylamlodipine have also been investigated in methanol-d4 by 1H NMR spectroscopy and the agreement with the results by HPLC is good. The rate of detritylation increases with increasing concentrations of benzenesulfonic acid, and p-methoxy-substituents in the trityl group have been shown to lead to faster reactions. In methanol, the rate is hardly affected by 10 % (vol. fraction) chloroform. These studies relate to mechanistic investigations of acid-catalysed deaminations of methoxy-substituted tritylalkylamines, and Arrhenius activation parameters (Ea and A) are similar indicating a common generic mechanism. Acid-catalysed trans-esterification has been shown by HPLC to accompany detritylation in methanol, and attendant protium-deuterium exchange in the methyl at C6 by reversible acid-catalysed iminium ion formation in the 4-aryl-1,4-dihydropyridine moiety of both N-tritylamlodipine and amlodipine has been investigated in deuteriated methanol by 1H, 13C, and 15N NMR spectroscopy.

TWO CRYSTALLINE HYDRATE FORMS OF AMLODIPINE BENZENESULFONATE OF HIGH PURITY, PROCESSES FOR THEIR PREPARATION AND USE

The novel crystalline amlodipine benzenesulfonate dihydrate of high purity is disclosed, as well as the process for preparation of the novel crystalline amlodipine benzenesulfonate dihydrate of high purity and the crystalline amlodipine benzenesulfonate monohydrate of high purity, suitable for the preparation of pharmaceutical formulations for the treatment of cardiac diseases or hypertension, and their use as intermediate compounds in the improved process of purification of the nonhydrate benzenesulfonate (besylate) salt of amlodipine.The process for preparation of the crystalline amlodipine benzenesulfonate dihydrate is carried in the way that from the C1-C5 alcoholic solution of amlodipine benzenesulfonate with water while stirring at a temperature of 20°C or lower the crystals of pure amlodipine benzenesulfonate dihydrate are separated, and isolated.The process for preparation of the crystalline amlodipine benzenesulfonate monohydrate is carried in the way that from the C1-C5 alcoholic solution of amlodipine benzenesulfonate with water while stirring at a temperature of 30°C or higher the crystals of pure amlodipine benzenesulfonate monohydrate are separated, and isolated.