(R)-2-PHENYLPIPERIDINE Chemical Properties

Boiling point:

257.3±19.0 °C(Predicted)

Density 

0.967±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

liquid

pka

9.74±0.10(Predicted)

Safety Information

HS Code 

2933399990

(R)-2-PHENYLPIPERIDINE Usage And Synthesis

Description

(R)-2-Phenylpiperidine is an alkene that has been used in the desymmetrization of secondary amides to produce enantiopure products. It has been shown to be stereoselective. It could prepared from δ-Amino β-keto esters 3. The kinetic resolution of this compound is due to the formation of an enamine, which undergoes a 1,4-addition reaction with an aldoxime or piperidone.

Uses

Chiral building block developed using Liverpool ChiroChem-patented technology.

Synthesis

In a 10 mL one-necked round-bottomed flask equipped with a magnetic stir bar, rubber septum, and argon balloon was placed 0.033 g (0.19 mmol, 1 equiv.) of (R)-(+)-6-Phenylpiperidin-2-one and THF (1.2 mL). Lithium aluminum hydride (0.95 mL, 1.0 M solution in THF, 0.95 mmol) was added slowly via syringe and the reaction mixture was stirred at rt for 8 h. The solution was cooled to 0 °C, sat. Na2SO4 (0.17 mL) was added, stirred for 0.5 h at rt and the reaction mixture was filtered through Celite. The organic phases were concentrated and flash chromatography (7% MeOH/CH2Cl2) gave 0.025 g (82%) of (R)-2-phenylpiperidine as volatile oil.

(R)-2-PHENYLPIPERIDINE(58613-54-0)Related Product Information

• (R)-(+)-2-PHENOXYPROPIONIC ACID
• (R)-2-methyl-2-phenylpiperidine
• (S)-2-PHENYLPIPERIDINE