L-erythro-Methylphenidate Hydrochloride

Base Information

• Chemical Name: L-erythro-Methylphenidate Hydrochloride
• CAS No.: 29419-97-4
• Molecular Formula: C₁₄H₁₉NO₂*ClH
• Molecular Weight: 269.771
• DSSTox Substance ID: DTXSID10436715
• ChEMBL ID: CHEMBL50570
• Mol file: 29419-97-4.mol

Synonyms:CHEMBL50570;29419-97-4;L-erythro-Methylphenidate Hydrochloride;DTXSID10436715;AKOS015911483

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Chemical Property of L-erythro-Methylphenidate Hydrochloride

Chemical Property:

• Melting Point: 218-219 °C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 269.1182566
• Heavy Atom Count: 18
• Complexity: 249

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C(C1CCCCN1)C2=CC=CC=C2.Cl
• Isomeric SMILES: COC(=O)[C@@H]([C@@H]1CCCCN1)C2=CC=CC=C2.Cl
• Uses: Controlled substance. The erythro isomers have been shown to exhibit very little therapeutic effect and contribute mainly to the toxic hypertensive effects of this drug.

Technology Process of L-erythro-Methylphenidate Hydrochloride

There total 15 articles about L-erythro-Methylphenidate Hydrochloride 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: 100.0%

methanol (67-56-1) + (R*,R*)-7-phenyl-1-azabicyclo[4.2.0]octan-8-one → 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)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo982214t

Reference yield: 95.0%

methanol (67-56-1) + 2-phenyl-2-(piperidin-2-yl)acetic acid (1076192-92-1,54631-24-2,744954-37-8) → 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)

Guidance literature:

methanol; 2-phenyl-2-(piperidin-2-yl)acetic acid; With hydrogenchloride; at 69.4 ℃;

With Trimethyl orthoacetate; at 60 - 63 ℃; Product distribution / selectivity;

Reference yield: 89.0%

methanol (67-56-1) + threo-ritalinic acid (1076192-92-1,54631-24-2,744954-37-8) → threo-methyl α-phenyl-α-(2-piperidyl)acetate 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)

Guidance literature:

methanol; threo-ritalinic acid; thionyl chloride; In water; ethyl acetate; at 0 - 20 ℃;

With hydrogenchloride; In isopropyl alcohol; at 0 - 25 ℃; for 4 - 6h;

upstream raw materials:

methanol

threo-ritalinic acid

dl-threo-methylphenidate

methyl (R*)-2-phenyl-2-((S*)-piperidin-2-yl)acetate

Downstream raw materials:

methyl (S,S)-1-phenyl-2-[N-(1')-piperidin-2'-yl]ethanoate hydrochloride

2-phenyl-2-(piperidin-2-yl)acetic acid

d-Ritalinic acid

l-threo-methylphenidate / dibenzoyl L-tartaric acid

Refernces

• 1、 -. "IMPROVEMENTS IN OR RELATING TO ORGANIC MATERIAL". Paragraph 0056; 0057. . Retrieved 2018/04/13.
• 2、 -. "LOW-TEMPERATURE SYNTHESIS OF METHYLPHENIDATE HYDROCHLORIDE". Page/Page column 25. . Retrieved 2012/06/30.