4-(3-Methoxyphenyl)-1-methylpiperidine-4-carbonitrile

Base Information

• Chemical Name: 4-(3-Methoxyphenyl)-1-methylpiperidine-4-carbonitrile
• CAS No.: 5460-79-7
• Molecular Formula: C14H18 N2 O
• Molecular Weight: 230.31
• Hs Code.: 2933399090
• European Community (EC) Number: 226-742-7
• NSC Number: 21330
• UNII: NNP3VEH42Y
• DSSTox Substance ID: DTXSID80203037
• Nikkaji Number: J210.524A
• Wikidata: Q69757030
• ChEMBL ID: CHEMBL1605008
• Mol file: 5460-79-7.mol

Synonyms:5460-79-7;4-(3-Methoxyphenyl)-1-methylpiperidine-4-carbonitrile;1-Methyl-4-cyano-4-(3-methoxyphenyl)piperidine;1-Methyl-4-cyano-4-(3-methoxyphenyl)-piperidine;4-(3-Methoxyphenyl)-1-methyl-4-piperidinecarbonitrile;NSC21330;NSC 21330;NNP3VEH42Y;4-Cyano-4-(3-methoxyphenyl)-1-methylpiperidine;EINECS 226-742-7;NSC-21330;4-Piperidinecarbonitrile, 4-(3-methoxyphenyl)-1-methyl-;UNII-NNP3VEH42Y;4-Cyano-4-m-methoxyphenyl-1-methylpiperidine;MLS000719094;4-(3-methoxyphenyl)-1-methyl-piperidine-4-carbonitrile;CHEMBL1605008;SCHEMBL11814914;DTXSID80203037;HMS2713I16;AC-604;MFCD05857265;STK666079;AKOS000643874;SDCCGSBI-0139680.P001;NCGC00245444-01;SMR000291362;TS-03283;6-Acetylpyridine-2-carboxylicacidethylester;CS-0312753;FT-0647371;D85582;W-203057;ISONIPECOTONITRILE, 4-(M-METHOXYPHENYL)-1-METHYL-

Chemical Property of 4-(3-Methoxyphenyl)-1-methylpiperidine-4-carbonitrile

Chemical Property:

• Vapor Pressure: 6.87E-06mmHg at 25°C
• Melting Point: 43-47°C
• Boiling Point: 377.2°Cat760mmHg
• PKA: 6.56±0.10(Predicted)
• Flash Point: 181.9°C
• PSA: 36.26000
• Density: 1.1g/cm³
• LogP: 2.12008
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 230.141913202
• Heavy Atom Count: 17
• Complexity: 299

Purity/Quality:

99%, ^*data from raw suppliers

4-(3-Methoxyphenyl)-1-methyl-4-piperidinecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(CC1)(C#N)C2=CC(=CC=C2)OC
• Uses: 4-Cyano-4-(3-methoxyphenyl)-1-methylpiperidine is an aryl piperidine derivative used in the preparation of 1,4-diarylpiperidine-4-methylureas as anti-hyperlipidemic agents.

Technology Process of 4-(3-Methoxyphenyl)-1-methylpiperidine-4-carbonitrile

There total 7 articles about 4-(3-Methoxyphenyl)-1-methylpiperidine-4-carbonitrile 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: 63.0%

3-methoxyphenylacetonitrile (19924-43-7) + mechlorethamine hydrochloride (55-86-7) → 1-methyl-4-(m-methoxyphenyl)-4-cyanopiperidine (5460-79-7)

Guidance literature:

With sodium hydroxide; cetyltributylphosphonium bromide; at 100 ℃; for 1h;

DOI:10.1002/jhet.5570230115

Reference yield:

4-hydroxy-2-(2-hydroxyethyl)-2-(3-methoxyphenyl)butanenitrile (620593-93-3) + methylamine (74-89-5) → 1-methyl-4-(m-methoxyphenyl)-4-cyanopiperidine (5460-79-7)

Guidance literature:

4-hydroxy-2-(2-hydroxyethyl)-2-(3-methoxyphenyl)butanenitrile; With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In ethyl acetate; at -30 ℃;

methylamine; With N-ethyl-N,N-diisopropylamine; at -30 - 20 ℃;

DOI:10.1016/j.bmcl.2009.01.020

Reference yield:

N-Methyldiethanolamine (105-59-9) → 1-methyl-4-(m-methoxyphenyl)-4-cyanopiperidine (5460-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / CHCl₃ / 1 h / Heating

2: 63 percent / hexadecyltributylphosphonium bromide, 50percent aq. NaOH / 1 h / 100 °C

With sodium hydroxide; thionyl chloride; cetyltributylphosphonium bromide; In chloroform;

DOI:10.1002/jhet.5570230115

upstream raw materials:

3-methoxyphenylacetonitrile

nitrogen mustard

mechlorethamine hydrochloride

N-Methyldiethanolamine

Downstream raw materials:

1-[4-(3-methoxy-phenyl)-1-methyl-piperidin-4-yl]-propan-1-one

1-[4-(3-methoxy-phenyl)-1-methyl-[4]piperidyl]-ethanone

C-[4-(3-methoxy-phenyl)-1-methyl-[4]piperidyl]-methylamine

4-(3-hydroxy-phenyl)-1-methyl-piperidine-4-carboxylic acid

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR TREATMENT OF SEVERE PAIN". Paragraph 0097; 0098. . Retrieved 2013/12/03.
• 2、 Mercer, Susan L.,Cunningham, Christopher W.,Eddington, Natalie D.,Coop, Andrew. "Opioids and efflux transporters. Part 3: P-glycoprotein substrate activity of 3-hydroxyl addition to meperidine analogs". body text. p. 3638 - 3640. Retrieved 2009/04/11.