54631-24-2

Usage

Uses

A metabolite

Upstream product

• 19395-39-2 (±)-erythro/threo-2-phenyl-2-(piperidin-2-yl)acetamide 
• 298-59-9 methylphenidate hydrochloride 
• 40572-71-2 threo-(-)-Methylphenidate 
• 19395-39-2 dl-erythro-α-phenyl-α-(2-piperidyl)acetamide 
• 129389-68-0 l-ritalinic acid 
• 2700-22-3 Benzylidenemalononitrile 
• 618-42-8 1-piperidin-1-yl-ethanone 
• 5005-36-7 phenyl-pyridin-2-yl-acetonitrile 
• 7251-52-7 2-phenyl-2-(pyridin-2-yl)acetamide 

Downstream Products

• 1382859-13-3 d-threo-ritalinic acid hydrochloride 
• 851895-37-9 l-threo-ritalinic acid hydrochloride 
• 64407-57-4 N,N-dicyclohexylurea 

Relevant academic research and scientific papers

Microtubing-Reactor-Assisted Aliphatic C?H Functionalization with HCl as a Hydrogen-Atom-Transfer Catalyst Precursor in Conjunction with an Organic Photoredox Catalyst

Chlorine radical, which is classically generated by the homolysis of Cl2 under UV irradiation, can abstract a hydrogen atom from an unactivated C(sp3)?H bond. We herein demonstrate the use of HCl as an effective hydrogen-atom-transfer catalyst precursor activated by an organic acridinium photoredox catalyst under visible-light irradiation for C?H alkylation and allylation. The key to success relied on the utilization of microtubing reactors to maintain the volatile HCl catalyst. This photomediated chlorine-based C?H activation protocol is effective for a variety of unactivated C(sp3)?H bond patterns, even with primary C(sp3)?H bonds, as in ethane. The merit of this strategy is illustrated by rapid access to several pharmaceutical drugs from abundant unfunctionalized alkane feedstocks.

AN IMPROVED PROCESS FOR THE PREPARATION OF DEXMETHYL PHENIDATE HYDROCHLORIDE

Disclosed herein a process for the preparation of highly pure dexmethylphenidate hydrochloride (Formula-I) which comprises the steps of neutralization of dl- threomethylphenidate hydrochloride to dl-threo methylphenidate; subsequent resolution of dl-threo methylphenidate using amino acid or its derivatives as chiral resolution agent to yield dexmethylphenidate salt; hydrolysis of the salt and further conversion of dexmethylphenidate into its hydrochloride salt.

Preparation and structural analysis of (±)-threo-ritalinic acid

Hydrolysis of the methyl ester (±)-threo-methyl phenidate afforded the free acid in 40% yield, viz. (±)-threo-ritalinic acid, C 13H17NO2. Hydrolysis and subsequent crystallization were accomplished at pH values between 5 a

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.

A PROCESS FOR THE PREPARATION OF ALPHA-ARYL-ALPHA-PIPERID-2-YL-ACETAMIDES AND THE ACID HYDROLYSIS THEREOF

A process for the preparation of -aryl--piperid-2-yl-acetamides of formula (I) in which Ar is as defined in the disclosure, by catalytic reduction of α-aryl-α-pyridin-2-yl-acetamides (II) with rhodium catalysts. Acetamides of formula (II) can subsequently by hydrolysed to the corresponding arylacetic acids, e. g. ritalinic acid, a direct precursor of methylphenidate.

Method to separate stereoisomers

A method to resolve the stereoisomers of an optically active compound comprising an amine moiety. The method provides a mixture comprising two stereoisomers of a compound comprising a amine moiety. The method supplies l-fenchyloxyacetic acid, treats the mixture of stereoisomers with that l-fenchyloxyacetic acid, and collects one of those two stereoisomers having greater than a 99 percent enantiomeric excess.

Enzymatic resolution of (±)-threo-methylphenidate

The resolution of (±)-threo-methylphenidate by enzymatic hydrolysis with α-chymotrypsin or subtilisin carlsberg to afford (2S,2'S)-(-)-threo and (2R,2'R)-(+)-threo-methylphenidate hydrochlorides in high enantiomeric purities is described.

Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs

As part of a program, to develop medications which can block the binding of cocaine to the dopamine transporter, yet spare dopamine uptake, a series of aromatic ring-substituted methylphenidate derivatives was synthesized and tested for inhibitory potency in [3H]WIN 35,428 binding and [3H]dopamine uptake assays using rat striatal tissue. Synthesis was accomplished by alkylation of 2-bromopyridine with anions derived from various substituted phenylacetonitriles. In most cases, erythro compounds were markedly less potent than the corresponding (±)-threo-methylphenidate (TMP; Ritalin) derivatives. The ortho-substituted compounds were much less potent than the corresponding meta- and/or para-substituted derivatives. The most potent compound against [3H]WIN 35,428 binding, m-bromo-TMP, was 20-fold more potent than the parent compound, whereas the most potent compound against [3H]dopamine uptake, m,p-dichloro-TMP, was 32-fold more potent. Threo derivatives with m-or p-halo substituents were more potent than TMP, while electron-donating substituants caused little change or a small loss of potency. All of the derivatives had Hill coefficients approaching unity, except m,p-dichloro-TMP, which had an nH of 2.0. Although the potency of the (±)-methylphenidate derivatives in the two assays was highly correlated (R2 = 0.986), the compounds m-chloro-, m-methyl-, and p-iodo-TMP were 4-5-fold more potent at inhibiting [3H]-WIN 35,428 binding than [3H]dopamine uptake (cocaine has a ratio of 2.3). These and other compounds may be promising candidates for further testing as potential partial agonists or antagonists of cocaine.