Bicifadine

Base Information

• Chemical Name: Bicifadine
• CAS No.: 71195-57-8
• Molecular Formula: C12H15 N
• Molecular Weight: 173.258
• Hs Code.: 2933990090
• European Community (EC) Number: 615-260-6
• DSSTox Substance ID: DTXSID20867995
• Wikipedia: Bicifadine
• Wikidata: Q4903628
• NCI Thesaurus Code: C79930
• Pharos Ligand ID: 87HY658QHBRA
• Metabolomics Workbench ID: 149319
• ChEMBL ID: CHEMBL511099
• Mol file: 71195-57-8.mol

Synonyms:bicifadine;bicifadine hydrochloride

Chemical Property of Bicifadine

Chemical Property:

• Vapor Pressure: 0.0048mmHg at 25°C
• Boiling Point: 276.4°C at 760 mmHg
• Flash Point: 125°C
• PSA: 12.03000
• Density: 1.091g/cm³
• LogP: 2.18470
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 173.120449483
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

1-(p-Tolyl)-3-azabicyclo[3.1.0]hexane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C23CC2CNC3
• Recent ClinicalTrials: A 52-Week Study of Bicifadine in Patients With Chronic Neuropathic Pain Associated With Diabetic Peripheral Neuropathy
• Recent EU Clinical Trials: An Open-label 52-Week Safety Study of Bicifadine SR in Adult Outpatients with Chronic Neuropathic Pain Associated with Diabetic Peripheral Neuropathy
• Uses: Analgesic.

Technology Process of Bicifadine

There total 5 articles about Bicifadine 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: 58.0%

(+/-)-1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexan-2,4-dione (66504-87-8,66504-77-6) → bicifadine (71195-57-8)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In benzene; for 2h; Heating;

DOI:10.1021/jm00137a002

Reference yield:

methyl bromo(4-methylphenyl)acetate (77053-52-2,66505-09-7) → bicifadine (71195-57-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / NaOMe / diethyl ether / 24 h / Ambient temperature

2: 80 percent / KOH / ethanol; H₂O / 6 h / Heating

3: 70 percent / urea / xylene / Heating

4: 58 percent / sodium bis(2-methoxyethoxy)aluminum hydride / benzene / 2 h / Heating

With potassium hydroxide; sodium methylate; sodium bis(2-methoxyethoxy)aluminium dihydride; urea; In diethyl ether; ethanol; water; xylene; benzene;

DOI:10.1021/jm00137a002

Reference yield:

2-bromo-2-(p-tolyl)acetyl chloride → bicifadine (71195-57-8)

Guidance literature:

Multi-step reaction with 5 steps

2: 86 percent / NaOMe / diethyl ether / 24 h / Ambient temperature

3: 80 percent / KOH / ethanol; H₂O / 6 h / Heating

4: 70 percent / urea / xylene / Heating

5: 58 percent / sodium bis(2-methoxyethoxy)aluminum hydride / benzene / 2 h / Heating

With potassium hydroxide; sodium methylate; sodium bis(2-methoxyethoxy)aluminium dihydride; urea; In diethyl ether; ethanol; water; xylene; benzene;

DOI:10.1021/jm00137a002

upstream raw materials:

(+/-)-1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexan-2,4-dione

methyl bromo(4-methylphenyl)acetate

(1R,2S)-1-p-Tolyl-cyclopropane-1,2-dicarboxylic acid dimethyl ester

Downstream raw materials:

3-methyl-1-(4-methylphenyl)-3-azabicyclo<3.1.0>hexane

3-Allyl-1-(p-tolyl)-3-azabicyclo<3.1.0>hexan

3-(n-hexyl)-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

3-Methyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

Refernces

• 1、 -. "Method of treating depression using azabicyclohexanes". . . Retrieved 2008/06/13.