3-Phenyl-3-(N-piperidinyl)bicyclo(3.1.0)hexane

Base Information

• Chemical Name: 3-Phenyl-3-(N-piperidinyl)bicyclo(3.1.0)hexane
• CAS No.: 114200-20-3
• Molecular Formula: C17H23 N
• Molecular Weight: 241.376
• Nikkaji Number: J522.684H,J522.685F
• ChEMBL ID: CHEMBL343429,CHEMBL347761
• Mol file: 114200-20-3.mol

Synonyms:3-phenyl-3-(N-piperidinyl)bicyclo(3.1.0)hexane;3-phenyl-3-(N-piperidinyl)bicyclo(3.1.0)hexane hydrochloride, (cis)-isomer;3-phenyl-3-(N-piperidinyl)bicyclo(3.1.0)hexane, (trans)-isomer;3-PPBH

Chemical Property of 3-Phenyl-3-(N-piperidinyl)bicyclo(3.1.0)hexane

Chemical Property:

• Vapor Pressure: 0.0001mmHg at 25°C
• Boiling Point: 338.2°Cat760mmHg
• Flash Point: 143.5°C
• PSA: 3.24000
• Density: 1.09g/cm³
• LogP: 3.73560
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 241.183049738
• Heavy Atom Count: 18
• Complexity: 289

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)C2(CC3CC3C2)C4=CC=CC=C4
• Isomeric SMILES: C1CCN(CC1)C2(C[C@H]3C[C@H]3C2)C4=CC=CC=C4

Technology Process of 3-Phenyl-3-(N-piperidinyl)bicyclo(3.1.0)hexane

There total 4 articles about 3-Phenyl-3-(N-piperidinyl)bicyclo(3.1.0)hexane 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: 86.0%

1,5-dibromo-pentane (111-24-0) + cis-3-phenyl-3-aminobicyclo<3.1.0>hexane (114200-24-7) → cis-2-phenyl-2-(N-piperidinyl)bicyclo<3.1.0>hexane (114200-20-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 48h;

DOI:10.1021/jm00403a014

Reference yield:

(1R,3r,5S)-bicyclo[3.1.0]hexan-3-ol (694-43-9,89489-26-9) → cis-2-phenyl-2-(N-piperidinyl)bicyclo<3.1.0>hexane (114200-20-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / chromic acid / diethyl ether / 3 h / Ambient temperature

2: 42 percent / diethyl ether; cyclohexane / 1.) -70 deg C, 10 min, 2.) 20 deg C, 20 min

3: 1.) sodium azide, trifluoroacetic acid, 2. ) LAH / 1.) CHCl₃, room temperature, 4 h, 2.) ether, reflux, 3 h

4: 86 percent / K₂CO₃ / dimethylformamide / 48 h / 60 °C

With lithium aluminium tetrahydride; sodium azide; chromic acid; potassium carbonate; trifluoroacetic acid; In diethyl ether; cyclohexane; N,N-dimethyl-formamide;

DOI:10.1021/jm00403a014

Reference yield:

bicyclo[3.1.0]hexan-3-one (1755-04-0) → cis-2-phenyl-2-(N-piperidinyl)bicyclo<3.1.0>hexane (114200-20-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 42 percent / diethyl ether; cyclohexane / 1.) -70 deg C, 10 min, 2.) 20 deg C, 20 min

2: 1.) sodium azide, trifluoroacetic acid, 2. ) LAH / 1.) CHCl₃, room temperature, 4 h, 2.) ether, reflux, 3 h

3: 86 percent / K₂CO₃ / dimethylformamide / 48 h / 60 °C

With lithium aluminium tetrahydride; sodium azide; potassium carbonate; trifluoroacetic acid; In diethyl ether; cyclohexane; N,N-dimethyl-formamide;

DOI:10.1021/jm00403a014

upstream raw materials:

1,5-dibromo-pentane

cis-3-phenyl-3-aminobicyclo<3.1.0>hexane

(1R,3r,5S)-bicyclo[3.1.0]hexan-3-ol

bicyclo[3.1.0]hexan-3-one