Dexmethylphenidate

Base Information

• Chemical Name: Dexmethylphenidate
• CAS No.: 40431-64-9
• Molecular Formula: C14H19NO2
• Molecular Weight: 233.31
• Hs Code.: 2933399090
• UNII: M32RH9MFGP
• DSSTox Substance ID: DTXSID70893769
• Nikkaji Number: J343.157F
• Wikipedia: Dexmethylphenidate
• Wikidata: Q1207210
• NCI Thesaurus Code: C26642
• RXCUI: 352372
• Pharos Ligand ID: AS1JHQZZ1QM7
• Metabolomics Workbench ID: 43682
• ChEMBL ID: CHEMBL827
• Mol file: 40431-64-9.mol

Synonyms:Dexmethylphenidate;Dexmethylphenidate Hydrochloride;Focalin;Focalin XR;Hydrochloride, Dexmethylphenidate;XR, Focalin

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Chemical Property of Dexmethylphenidate

Chemical Property:

• Boiling Point: 327.6±17.0 °C(Predicted)
• PKA: 9.51±0.10(Predicted)
• PSA: 38.33000
• Density: 1.070±0.06 g/cm3(Predicted)
• LogP: 2.41410
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 233.141578849
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1CCCCN1)C2=CC=CC=C2
• Isomeric SMILES: COC(=O)[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2
• Recent ClinicalTrials: Fed-Fast Crossover Study to Assess the Effect of Food With CTx-1301 in Healthy Subjects
• Uses: Treatment of attention deficit/hyperactivity disorder.

Technology Process of Dexmethylphenidate

There total 83 articles about Dexmethylphenidate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

methylphenidate hydrochloride (298-59-9,19262-68-1,23644-60-2,23655-65-4,29419-95-2,29419-96-3,29419-97-4,56502-30-8) → dl-threo-methylphenidate (113-45-1,20748-11-2,20748-12-3,40431-62-7,40431-63-8,40431-64-9,40572-71-2,52703-69-2,52760-39-1,132831-06-2)

Guidance literature:

With ammonium hydroxide; In water; pH=~ 9;

Reference yield: 75.0%

methyl threo-2-phenyl-2-(N-methoxycarbonyl-2'-piperidyl)acetate → dl-threo-methylphenidate (113-45-1,20748-11-2,20748-12-3,40431-62-7,40431-63-8,40431-64-9,40572-71-2,52703-69-2,52760-39-1,132831-06-2)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ol9905046

Reference yield: 65.0%

methanol (67-56-1) + (Z)-3-Amino-7-methanesulfonyloxy-2-phenyl-hept-2-enoic acid methyl ester (460356-15-4) → dl-threo-methylphenidate (113-45-1,20748-11-2,20748-12-3,40431-62-7,40431-63-8,40431-64-9,40572-71-2,52703-69-2,52760-39-1,132831-06-2) + methyl (R*)-2-phenyl-2-((S*)-piperidin-2-yl)acetate (113-45-1,20748-11-2,20748-12-3,40431-62-7,40431-63-8,40431-64-9,40572-71-2,52703-69-2,52760-39-1,132831-06-2)

Guidance literature:

(Z)-3-Amino-7-methanesulfonyloxy-2-phenyl-hept-2-enoic acid methyl ester; With hydrogenchloride; bromocresol green; sodium cyanoborohydride; In methanol; pH=6;

With potassium hydroxide; Heating;

methanol; With thionyl chloride;

DOI:10.1016/S0223-5234(01)01230-2

upstream raw materials:

methanol

Ritalinic acid

piperidine

Methyl phenyldiazoacetate

Downstream raw materials:

(+/-)-threo-Ritalinol

dexmethylphenidate hydrochloride

Refernces

• 1、 Kim, Jae Hyun,Paul, Anirudra,Ghiviriga, Ion,Seidel, Daniel. "α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines". supporting information. p. 797 - 801. Retrieved 2021/02/06.
• 2、 -. "Methylphenidate, right pai methyl ester preparation method, intermediate and preparation method". . . Retrieved 2019/04/30.