29419-97-4

Basic information

• Product Name: D-erythro-Methylphenidate Hydrochloride
• Synonyms: (2R,2'S)-(+)-threo-Methyl α-Phenyl-α-(2-piperidyl)acetate Hydrochloride;(αR,2S)-
• CAS NO: 29419-97-4
• Molecular Formula: C₁₄H₁₉NO₂*ClH
• Molecular Weight: 269.7671
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 29419-97-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 218-219 °C
• Appearance: /
• CAS DataBase Reference: D-erythro-Methylphenidate Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: D-erythro-Methylphenidate Hydrochloride(29419-97-4)
• EPA Substance Registry System: D-erythro-Methylphenidate Hydrochloride(29419-97-4)

Safety Data

• Hazardous Substances Data: 29419-97-4(Hazardous Substances Data)

Usage

Description

D-erythro-Methylphenidate Hydrochloride is a pharmaceutical compound that belongs to the class of central nervous system stimulants. It is primarily used for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. D-erythro-Methylphenidate Hydrochloride is known for its ability to improve focus, attention, and impulse control in individuals with ADHD.

Uses

Used in Pharmaceutical Industry:
D-erythro-Methylphenidate Hydrochloride is used as a therapeutic agent for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It works by increasing the levels of certain neurotransmitters in the brain, such as dopamine and norepinephrine, which helps improve focus, attention, and impulse control.
However, it is important to note that the erythro isomers of this compound have been shown to exhibit very little therapeutic effect and contribute mainly to the toxic hypertensive effects of the drug. As a result, the dextro isomers are typically preferred for medical use.
Additionally, D-erythro-Methylphenidate Hydrochloride is classified as a controlled substance due to its potential for abuse and dependence. It is crucial to follow the prescribed dosage and administration guidelines to minimize the risk of adverse effects and ensure the safe and effective use of the medication.

Upstream product

• 67-56-1 methanol 
• 1076192-92-1 threo-ritalinic acid 
• 113-45-1 dl-threo-methylphenidate 
• 113-45-1 methyl (R*)-2-phenyl-2-((S*)-piperidin-2-yl)acetate 
• 1076192-92-1 2-phenyl-2-(piperidin-2-yl)acetic acid 
• 2629-91-6 7-phenyl-1-aza-bicyclo[4.2.0]octan-8-one 
• 81929-14-8 N-(2,2,2-trichloroethylidene)prop-2-en-1-amine 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 29419-95-2 methyl (S,S)-1-phenyl-2-[N-(1')-piperidin-2'-yl]ethanoate hydrochloride 
• 1076192-92-1 2-phenyl-2-(piperidin-2-yl)acetic acid 
• 1076192-92-1 d-Ritalinic acid 
• 40572-71-2 threo-(-)-Methylphenidate 
• 40431-64-9 dexmethylphenidate 
• 42510-61-2 (+/-)-threo-Ritalinol 
• 19130-92-8 (+/-)-threo-ritalinic acid hydrochloride 

Relevant articles and documents

Changing stereoselectivity and regioselectivity in copper(i)-catalyzed 5-: Exo cyclization by chelation and rigidity in aminoalkyl radicals: Synthesis towards diverse bioactive N-heterocycles

The work reveals that a chelate-Type interaction in the transition state of a β-Aminoalkyl radical in a copper(i)-catalyzed 5-exo-Trig radical cyclization step changes the usual stereochemistry of the NH-pyrrolidine ring predicted by the Beckwith-Houk transition state model. In contrast, the rigidity in the fused β-Aminoalkyl radical changes the Baldwin's predicted 5-exo to 6-endo cyclization mode, preferentially forming a piperidine ring over a pyrrolidine ring via a geometrically constrained transition state. The resultant diverse NH-pyrrolidines, pyrrolines and piperidines are sources of the bioactive natural product roseophilin and the drug Ritalin among others.

PROCESS FOR THE PREPARATION OF METHYLPHENIDATE AND PHARMACEUTICAL SALTS THEREOF

The present invention is directed to an improved process for the preparation of methylphenidate, stereoisomer, mixture of stereoisomers and pharmaceutically acceptable salts thereof, more particularly, the sulfate and hydrochloride salts of methylphenidate, di-threo-methylphenidate and dex-methylphenidate. Methods of removing or reducing the amount of impurities from the above described process are also disclosed.

PROCESS FOR PREPARING METHYL PHENIDATE HYDROCHLORIDE

Disclosed herein is a process for the preparation of methyl phenidate hydrochloride (Formula I), comprising the steps of; hydrolyzing α-phenyl-α-pipyridyl acetamide (Formula II) in presence of mineral acid at reflux temperature and subsequent neutralization to yield threo -α-phenyl-α-pipyridyl-2-acetic acid (Formula III) which in presence of acidic catalyst reacts with methanol followed by treatment with alcoholic hydrochloride solution produces methyl phenidate hydrochloride.