| Identification | Back Directory | [Name]
(R)-2-PHENYLPIPERIDINE | [CAS]
58613-54-0 | [Synonyms]
(R)-2-PHENYLPIPERIDINE
(2R)-2-phenylpiperidine
(R)-2-Phenylpiperidine 95%
(R)-(+)-6-phenylpiperidine
Piperidine, 2-phenyl-, (2R)- | [Molecular Formula]
C11H15N | [MDL Number]
MFCD06762593 | [MOL File]
58613-54-0.mol | [Molecular Weight]
161.24 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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. |
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