methyl (S)-phenyl[(S)-piperidin-2-yl]acetate

Base Information

• Chemical Name: methyl (S)-phenyl[(S)-piperidin-2-yl]acetate
• CAS No.: 20748-11-2
• Deprecated CAS: 52760-39-1,73790-87-1
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• UNII: 207ZZ9QZ49,IS6UTS8ES9
• DSSTox Substance ID: DTXSID501312263
• Nikkaji Number: J343.158D
• Wikidata: Q27122839
• NCI Thesaurus Code: C62045
• RXCUI: 6901
• Pharos Ligand ID: AS1ZHKH1VYVD
• Metabolomics Workbench ID: 57929
• ChEMBL ID: CHEMBL290634

Synonyms:Centedrin;Concerta;Daytrana;Equasym;Hydrochloride, Methylphenidate;Metadate;Methylin;Methylphenidate;Methylphenidate Hydrochloride;Phenidylate;Ritalin;Ritalin SR;Ritalin-SR;Ritaline;Tsentedrin

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Chemical Property of methyl (S)-phenyl[(S)-piperidin-2-yl]acetate

Chemical Property:

• 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

Technology Process of methyl (S)-phenyl[(S)-piperidin-2-yl]acetate

There total 59 articles about methyl (S)-phenyl[(S)-piperidin-2-yl]acetate 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:

methylphenidate hydrochloride