86718-70-9

Basic information

• Product Name: (+)-Cisapride
• Synonyms: (+)-cis-Apride;(+)-(R)-Cisapride
• CAS NO: 86718-70-9
• Molecular Formula: C₂₃H₂₉ClFN₃O₄
• Molecular Weight: 0
• Mol File: 86718-70-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Cisapride(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Cisapride(86718-70-9)
• EPA Substance Registry System: (+)-Cisapride(86718-70-9)

Safety Data

• Hazardous Substances Data: 86718-70-9(Hazardous Substances Data)

Usage

General Description

(+)-Cisapride is a prokinetic agent that works by stimulating the muscles in the gastrointestinal tract, helping to improve their movements and speed up the emptying of the stomach. It is often used to treat conditions such as gastroesophageal reflux disease (GERD) and gastroparesis. However, it has been associated with serious side effects, including irregular heartbeats and potential risks of heart rhythm disturbances, which has led to its withdrawal from the market in several countries. Despite its withdrawal, (+)-cisapride remains an important molecule for research and development of new drugs targeted at the gastrointestinal system.

Upstream product

• 7206-70-4 4-amino-5-chloro-2-methoxybenzoic acid 
• 503433-37-2 C₁₅H₂₃FN₂O₂ 
• 150007-96-8 C₁₁H₁₂ClNO₅ 
• 1129-78-8 1-(3-bromopropoxy)-4-fluorobenzene 
• 401502-00-9 N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine 
• 1345718-98-0 (3S,4R,αR)-N(1)-(3'-(4''-fluorophenoxy)propyl)-3-methoxy-4-[N-benzyl-N-(α-methylbenzyl)amino]piperidine 
• 1345718-97-9 (R,R,R)-N(1)-[3'-(4''-fluorophenoxy)propyl]-3-methoxy-4-[N-benzyl-N-(α-methylbenzyl)amino]piperidin-2-one 
• 1345718-96-8 (R,R,R)-N(1)-[3'-(4''-fluorophenoxy)propyl]-3-hydroxy-4-[N-benzyl-N-(α-methylbenzyl)amino]-piperidin-2-one 
• 1345718-95-7 tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate 
• 1345718-94-6 tert-butyl (E)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate 

Downstream Products

• 125557-41-7 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-(2-methanesulfinyl-ethoxy)-benzamide 
• 102671-13-6 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-(2-methylsulfanyl-ethoxy)-benzamide 
• 102671-04-5 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-hydroxy-benzamide 

Relevant articles and documents

Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4- aminopiperidin-2-ones: Application to the asymmetric synthesis of (+)-(3S,4R)-cisapride

The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl) amide to δ-(N-allylamino)-α,β-unsaturated esters, followed by N-deallylation and cyclisation of the resultant β,δ-diamino esters, gives the corresponding 4-aminopiperidin-2-ones as single diastereoisomers (>99:1 dr). Subsequent deprotonation with LiHMDS and functionalisation of the resultant lithium enolate gives 3,4-anti-3-substituted-4-aminopiperidin-2-ones in >99:1 dr. Alternatively, in situ oxidation of the intermediate lithium (Z)-β-amino enolates formed upon conjugate addition gives α-hydroxy-β,δ-diamino esters, which after N-deallylation and cyclisation gives the corresponding 3,4-syn-3-hydroxy-4-aminopiperidin-2-ones in >99:1 dr. The utility of this methodology was successfully demonstrated in a concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)- cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy)propyl]-3-methoxy- 4-(2?-methoxy-4?-amino-5?-chlorobenzamido)piperidine} in nine steps from commercially available starting materials with an overall yield of 19%.