R)-3-PHENYL PIPERIDINE Chemical Properties

Melting point:

179-181℃

Boiling point:

263.2±19.0 °C(Predicted)

Density 

0.967±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

10.01±0.10(Predicted)

color 

Colourless to light yellow / liquid

InChI

InChI=1S/C11H15N/c1-2-5-10(6-3-1)11-7-4-8-12-9-11/h1-3,5-6,11-12H,4,7-9H2/t11-/m0/s1

InChIKey

NZYBILDYPCVNMU-NSHDSACASA-N

SMILES

N1CCC[C@H](C2=CC=CC=C2)C1

Safety Information

HS Code 

2933399990

R)-3-PHENYL PIPERIDINE Usage And Synthesis

Uses

(R)-3-Phenylopiridine is an intermediate in the synthesis of niraparib. Niraparib (MK-4827), an anticancer drug developed by Tesaro Biosciences, is a novel, orally administered selective poly(ADP-ribose) polymerase (PARP) inhibitor. This drug works by interfering with DNA repair processes in cells, making tumors more sensitive to DNA-damaging chemotherapy drugs.

Synthesis

The general procedure for the synthesis of (R)-3-phenylpiperidine from 3-phenylpiperidine was as follows: 3-phenylpiperidine (1,100 g, 621.1 mmol) was dissolved in isopropanol (50 mL). Another D-tartaric acid (93.16 g, 622.2 mmol) was dissolved in isopropanol (200 mL). The isopropanol solution of D-tartaric acid was slowly added dropwise to the isopropanol solution of 3-phenylpiperidine and the reaction was stirred for 2 hours. After completion of the reaction, the tartaric acid salt was obtained by filtration. Subsequently, methanol (10 L) was added to the tartrate and heated until complete dissolution and then stirring was stopped. The solution was slowly cooled to room temperature and crystallized at -20°C for 7 days. White crystals were collected by filtration to give 29.7 g of white waxy solid (R)-3-phenylpiperidine in 29.7% yield.

References

[1] Patent: CN108203404, 2018, A. Location in patent: Paragraph 0147-0162

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