Benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate

Base Information

• Chemical Name: Benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate
• CAS No.: 80139-87-3
• Molecular Formula: C₃₃H₃₅FN₂O₂
• Molecular Weight: 510.652
• European Community (EC) Number: 279-404-6
• DSSTox Substance ID: DTXSID401000992
• Nikkaji Number: J320.236D
• Mol file: 80139-87-3.mol

Synonyms:80139-87-3;EINECS 279-404-6;benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate;Benzyl 1-(4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylate;SCHEMBL11399769;C33H35FN2O2;DTXSID401000992;C33-H35-F-N2-O2;1-[4-Cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic acid phenylmethyl ester

Chemical Property of Benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate

Chemical Property:

• Vapor Pressure: 7.8E-16mmHg at 25°C
• Boiling Point: 631.1°C at 760 mmHg
• Flash Point: 335.5°C
• PSA: 53.33000
• Density: 1.2g/cm³
• LogP: 6.49078
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 510.26825653
• Heavy Atom Count: 38
• Complexity: 825

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(CCC1(C2=CC=CC=C2)C(=O)OCC3=CC=CC=C3)C4CCC(CC4)(C#N)C5=CC=C(C=C5)F

Technology Process of Benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate

There total 6 articles about Benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate 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:

1-(4-fluorophenyl)-4-oxocyclohexanecarbonitrile (56326-98-8) + (3S,4R)-benzyl 3-methyl-4-phenylpiperidine-4-carboxylate → (3S,4R)-benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate (80139-87-3)

Guidance literature:

With sodium tris(acetoxy)borohydride; In dichloromethane; at 20 ℃; for 24h;

DOI:10.3390/molecules22111971

Reference yield:

(3S)-3-methyl-4-phenyl-1-tosylpiperidine-4-carboxylic acid → (3S,4R)-benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate (80139-87-3)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C

2: potassium diphenylphosphine / tetrahydrofuran / 3 h / -40 °C

3: sodium tris(acetoxy)borohydride / dichloromethane / 24 h / 20 °C

With sodium tris(acetoxy)borohydride; potassium carbonate; potassium diphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3390/molecules22111971

Reference yield:

(S)-1-({4-methyl-N-[2-(tosyloxy)ethyl]phenyl}sulfonamido)propan-2-yl-4-methyl benzenesulfonate → (3S,4R)-benzyl 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylate (80139-87-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium amide / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 3 h / 0 - 40 °C

2.1: potassium hydroxide / 44 h / 170 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: potassium diphenylphosphine / tetrahydrofuran / 3 h / -40 °C

5.1: sodium tris(acetoxy)borohydride / dichloromethane / 24 h / 20 °C

With sodium tris(acetoxy)borohydride; potassium carbonate; sodium amide; potassium diphenylphosphine; potassium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3390/molecules22111971

upstream raw materials:

(3S,4R)-benzyl 3-methyl-4-phenyl-1-tosylpiperidine-4-carboxylate

1-(4-fluorophenyl)-4-oxocyclohexanecarbonitrile

(S)-1-((2-hydroxyethyl)amino)propan-2-ol

Refernces