58613-54-0

Basic information

• Product Name: (R)-2-PHENYLPIPERIDINE
• Synonyms: (R)-2-PHENYLPIPERIDINE;(R)-(+)-6-phenylpiperidine;Piperidine, 2-phenyl-, (2R)-;(R)-2-Phenylpiperidine 95%
• CAS NO: 58613-54-0
• Molecular Formula: C₁₁H₁₅N
• Molecular Weight: 161.24
• Mol File: 58613-54-0.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 257.3±19.0 °C(Predicted)
• Appearance: /
• Density: 0.967±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.74±0.10(Predicted)
• CAS DataBase Reference: (R)-2-PHENYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-PHENYLPIPERIDINE(58613-54-0)
• EPA Substance Registry System: (R)-2-PHENYLPIPERIDINE(58613-54-0)

Safety Data

• Hazardous Substances Data: 58613-54-0(Hazardous Substances Data)

Usage

Uses

Chiral building block developed using Liverpool ChiroChem-patented technology.

Upstream product

• 57050-07-4 2-phenyl-3,4,5,6-tetrahydropyridine 
• 212560-70-8 (+)-(6R)-6-phenylpiperidin-2-one 
• 116437-42-4 (5-oxo-5-phenyl-pentyl)-carbamic acid tert-butyl ester 
• 108-86-1 bromobenzene 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 3466-80-6 2-phenylpiperidine 
• 141120-45-8 (R)-1-benzyl-2,3-dihydro-2-phenylpyridin-4(1H)-one 
• 100-58-3 phenylmagnesium bromide 
• 5259-98-3 5-chloropentan-1-ol 
• 1452523-62-4 (2R)-1-[(R)-2-methylpropane-2-sulfinyl]-2-phenylpiperidine 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 591-51-5 phenyllithium 
• 5414-21-1 5-bromopentan-1-nitrile 
• 141120-58-3 (2R)-N-benzyl-2-phenyl-4-piperidinone 

Downstream Products

• 1186336-27-5 R-trifluoroacetamide 
• 80988-38-1 (S)-(-)-1-methyl-2-phenylpiperidine 

Relevant articles and documents

Rapid Synthesis of α-Chiral Piperidines via a Highly Diastereoselective Continuous Flow Protocol

A practical continuous flow protocol has been developed using readily accessible N-(tert-butylsulfinyl)-bromoimine and Grignard reagents, providing various functionalized piperidines (34 examples) in superior results (typically >80% yield and with >90:10 dr) within minutes. The high-performance scale-up is smoothly carried out, and efficient synthesis of the drug precursor further showcases its utility. This flow process offers rapid and scalable access to enantioenriched α-substituted piperidines.

Chemoenzymatic Synthesis of Substituted Azepanes by Sequential Biocatalytic Reduction and Organolithium-Mediated Rearrangement

Enantioenriched 2-aryl azepanes and 2-arylbenzazepines were generated biocatalytically by asymmetric reductive amination using imine reductases or by deracemization using monoamine oxidases. The amines were converted to the corresponding N′-aryl ureas, which rearranged on treatment with base with stereospecific transfer of the aryl substituent to the 2-position of the heterocycle via a configurationally stable benzyllithium intermediate. The products are previously inaccessible enantioenriched 2,2-disubstituted azepanes and benzazepines.

Synthesis of chiral cyclic amines via Ir-catalyzed enantioselective hydrogenation of cyclic imines

A highly enantioselective hydrogenation of cyclic imines for synthesis of chiral cyclic amines has been realized. With the complex of iridium and (R,R)-f-spiroPhos as the catalyst, a range of cyclic 2-aryl imines were smoothly hydrogenated under mild conditions without any additive to provide the corresponding chiral cyclic amines with excellent enantioselectivities of up to 98% ee. Moreover, this method could be successfully applied to the synthesis of (+)-(6S,10bR)-McN-4612-Z.