BENZYL 4-(BROMOMETHYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Chemical Properties

Melting point:

68 °C

Boiling point:

403.4±28.0 °C(Predicted)

Density 

1.356±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, stored under nitrogen

pka

-1.96±0.40(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C14H18BrNO2/c15-10-12-6-8-16(9-7-12)14(17)18-11-13-4-2-1-3-5-13/h1-5,12H,6-11H2

InChIKey

XJHKDSZGAWXUTB-UHFFFAOYSA-N

SMILES

N1(C(OCC2=CC=CC=C2)=O)CCC(CBr)CC1

CAS DataBase Reference

159275-17-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38-34

Safety Statements 

26-36/37/39-45

Hazard Note 

Irritant

HS Code 

2933399990

BENZYL 4-(BROMOMETHYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Usage And Synthesis

Synthesis

Under nitrogen atmosphere, benzyl 4-(hydroxymethyl)piperidine-1-carboxylate (10 g, 40.11 mmol) was added to a 500 mL three-necked round-bottomed flask, dissolved in dichloromethane (100 mL), and the mixture was cooled to 0 °C. Subsequently, a solution of triphenylphosphine (13.7 g, 52.14 mmol) in dichloromethane (50 mL) was slowly added to the reaction mixture and kept stirring at 0°C for 20 minutes. Next, a dichloromethane (50 mL) solution of carbon tetrabromide (16 g, 48.13 mmol) was added and the reaction mixture was brought to room temperature and stirred for 3 hours. Upon completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with deionized water. The organic layer was separated, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Finally, purification by column chromatography afforded benzyl 4-(bromomethyl)piperidine-1-carboxylate (10 g).

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3586 - 3604
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 13, p. 2606 - 2620
[3] Patent: WO2015/195950, A1. Location in patent: Page/Page column 82
[3] Patent: , 2015, . Location in patent: Page/Page column 82

BENZYL 4-(BROMOMETHYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE(159275-17-9)Related Product Information

• Benzyl formate
• BENZYL 4-(BROMOMETHYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE
• BENZYL (4-BROMOBUTYL)CARBAMATE