(S)-3-Phenylpiperidine

Base Information

• Chemical Name: (S)-3-Phenylpiperidine
• CAS No.: 59349-71-2
• Molecular Formula: C11H15N
• Molecular Weight: 161.247
• Hs Code.: 2933399090
• European Community (EC) Number: 261-713-2
• DSSTox Substance ID: DTXSID70208096
• Nikkaji Number: J308.670D
• Wikidata: Q72498254
• Mol file: 59349-71-2.mol

Synonyms:(S)-3-Phenylpiperidine;59349-71-2;(S)-3-Phenyl piperidine;(3s)-3-phenylpiperidine;(s)-3-phenyl-piperidine;EINECS 261-713-2;MFCD03839935;Piperidine, 3-phenyl-, (S)-;SCHEMBL383031;DTXSID70208096;AKOS015840988;AS-37479;A8352;CS-0171242;Q-102141

Chemical Property of (S)-3-Phenylpiperidine

Chemical Property:

• Vapor Pressure: 0.0104mmHg at 25°C
• Refractive Index: 1.522
• Boiling Point: 263.2 °C at 760 mmHg
• PKA: 10.01±0.10(Predicted)
• Flash Point: 115.5 °C
• PSA: 12.03000
• Density: 0.967 g/cm³
• LogP: 2.48240
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 161.120449483
• Heavy Atom Count: 12
• Complexity: 127

Purity/Quality:

99% ^*data from raw suppliers

(S)-3-Phenylpiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CNC1)C2=CC=CC=C2
• Isomeric SMILES: C1C[C@H](CNC1)C2=CC=CC=C2

Technology Process of (S)-3-Phenylpiperidine

There total 8 articles about (S)-3-Phenylpiperidine 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: 30.1%

3-phenylpiperidine (3973-62-4) → (S)-3-phenylpiperidine hydrochloride (59349-71-2)

Guidance literature:

With L-Tartaric acid; In isopropyl alcohol; for 2h; Reagent/catalyst; Solvent;

Reference yield:

3-phenylpiperidine (3973-62-4) → (S)-3-phenylpiperidine hydrochloride (59349-71-2) + (R)-3-phenyl piperidine (430461-56-6)

Guidance literature:

With (R)-10-camphorsulfonic acid; In ethanol; for 2h; Overall yield = 18.1 %; Overall yield = 18.1 g;

Reference yield:

1-benzyl-3-piperidone (40114-49-6) → (S)-3-phenylpiperidine hydrochloride (59349-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 2 h / 0 - 5 °C / Inert atmosphere

2.1: acetic acid; acetyl chloride / 1.5 h / Reflux

2.2: 16 h / 60 °C / 760.05 Torr / Autoclave

3.1: L-Tartaric acid / isopropyl alcohol / 2 h

With L-Tartaric acid; acetic acid; acetyl chloride; In tetrahydrofuran; isopropyl alcohol;

upstream raw materials:

3-phenylpiperidine

N-benzyl-3-phenylpiperidine

phenylmagnesium chloride

1-benzyl-3-piperidone

Downstream raw materials:

4-(3S-piperidine-3-yl)bromobenzene

(S)-3-(4-bromophenyl)piperidine-1-carboxylic acid tert-butyl ester

C₃₂H₃₆N₂O₃

Refernces

• 1、 Hansson,Waters,Holm,Sonesson. "On the quantitative structure-activity relationships of meta-substituted (S)-phenylpiperidines, a class of preferential dopamine D2 autoreceptor ligands: Modeling of dopamine synthesis and release in vivo by means of partial least squares regression". . p. 3121 - 3131. Retrieved 2007/10/02.