219915-67-0

Basic information

• Product Name: (E)-4-Methyl-N'-(2-oxo-1-phenyl-2-(piperidin-1-yl)ethylidene)benzenesulfonohydrazide
• Synonyms: (E)-4-Methyl-N'-(2-oxo-1-phenyl-2-(piperidin-1-yl)ethylidene)benzenesulfonohydrazide;1-(Phenylglyoxylyl)piperidine p-toluenesulfonylhydrazone;4-Methylbenzenesulfonic acid 2-[2-oxo-1-phenyl-2-(1-piperidinyl)ethylidene]hydrazide;4-methyl-N'-(2-oxo-1-phenyl-2-(piperidin-1-yl)ethylidene)benzenesulfonohydrazide
• CAS NO: 219915-67-0
• Molecular Formula: C₂₀H₂₃N₃O₃S
• Molecular Weight: 385.47992
• Mol File: 219915-67-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 543.4±43.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• PKA: 6.77±0.40(Predicted)
• CAS DataBase Reference: (E)-4-Methyl-N'-(2-oxo-1-phenyl-2-(piperidin-1-yl)ethylidene)benzenesulfonohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-Methyl-N'-(2-oxo-1-phenyl-2-(piperidin-1-yl)ethylidene)benzenesulfonohydrazide(219915-67-0)
• EPA Substance Registry System: (E)-4-Methyl-N'-(2-oxo-1-phenyl-2-(piperidin-1-yl)ethylidene)benzenesulfonohydrazide(219915-67-0)

Safety Data

• Hazardous Substances Data: 219915-67-0(Hazardous Substances Data)

Usage

General Description

"(E)-4-Methyl-N'-(2-oxo-1-phenyl-2-(piperidin-1-yl)ethylidene)benzenesulfonohydrazide" represents a specific organic chemical compound. It features notable elements such as carbon, hydrogen, nitrogen, sulfur, and oxygen within its molecular structure. (E)-4-Methyl-N'-(2-oxo-1-phenyl-2-(piperidin-1-yl)ethylidene)benzenesulfonohydrazide contains functional groups such as the ethylidene, sulfonohydrazide, and phenyl groups, along with a piperidine ring structure. Its precise composition and structure are crucial in deriving its chemical properties and potential applications. However, detailed information about its specific uses, toxicity, physical properties, or research related to this compound is not readily available.

Upstream product

• 110-89-4 piperidine 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 14377-63-0 1-(phenylglyoxylyl)piperidine 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 403502-85-2 7-phenyl-1-aza-bicyclo[4.2.0]octan-8-one 
• 2629-91-6 7-phenyl-1-azabicyclo<4.2.0>octan-8-one 

Relevant articles and documents

IMPROVEMENTS IN OR RELATING TO ORGANIC MATERIAL

The invention provides a method for the preparation of an intermediate for use in synthesizing a lower alkyl phenidate compound of formula (I), wherein each R1 independently represents an optionally substituted aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, acyl, carboxyl, hydroxyl, halogen, amino, nitro, sulfo or sulfhydryl group, R2 represents a hydrogen atom or a lower alkyl group, n represents an integer from 1 to 5 and m represents an integer from 1 to 3 or a pharmaceutically acceptable salt thereof; which method comprises the steps of: (a) flowing a tosylhydrazone compound of formula (IV), wherein R1, n and m are as defined above in relation to the methylphenidate of formula (I), an organic base and an organic solvent into a fluidic network; and (b) reacting the tosylhydrazone compound of formula (IV) and the base in the fluidic network under thermal and/or photochemical conditions to form a transient diazoamide compound of formula (V), wherein R1, n and m are as defined above in relation to the methylphenidate of formula (I).

Process for the preparation of dexmethylphenidate hydrochloride

The present invention provides a new and efficient process for the preparation of the dexmethylphenidate hydrochloride with high optical purity, the process comprising: (a) reacting a solution of threo-N-Boc-ritalinic acid with (S)-1-phenylethylamine, separating precipitated solid salt of (R,R)-enriched N-Boc-ritalinic acid with (S)-1-phenylethylamnine from the reaction mixture and recrystallizing, reslurring and/or trituring of said salt; (b) mixing the solid salt of (R,R)-N-Boc-ritalinic acid and (S)-1-phenylethylamine obtained in step (a) with aqueous acid and separating (R,R)-N-Boc-ritalinic acid from the mixture; and (c) reacting the (R,R)-N-Boc-ritalinic acid prepared in step (b) with hydrogen chloride and methanol to give dexmethylphenidate hydrochloride with optical purity of at least 99% ee. The present invention further provides salt of (R,R)-N-Boc-ritalinic acid with (S)-1-phenylethylamine as new intermediate in the preparation of dexmethylphenidate hydrochloride.