METHYL 1-BENZYLPIPERIDINE-4-CARBOXYLATE Chemical Properties

Boiling point:

115 °C

Density 

1.093±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

7.86±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C14H19NO2/c1-17-14(16)13-7-9-15(10-8-13)11-12-5-3-2-4-6-12/h2-6,13H,7-11H2,1H3

InChIKey

MXOZSPRDEKPWCW-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCC(C(OC)=O)CC1

CAS DataBase Reference

10315-06-7(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

29333990

METHYL 1-BENZYLPIPERIDINE-4-CARBOXYLATE Usage And Synthesis

Uses

The preparation of donepezil hydrochloride using 1-benzyl-4-piperidinecarboxaldehyde as an intermediate has been widely studied and applied. Donepezil hydrochloride is a long-acting symptomatic treatment for Alzheimer's disease (AD).

Chemical Properties

Colorless liquid

Synthesis

Methyl 4-piperidinecarboxylate (10.00 g, 6.4 mmol) and triethylamine (10.32 g, 10.2 mmol) were dissolved in chloroform (100 mL), and benzyl bromide (14.69 g, 8.6 mmol) was slowly added under argon protection while the reaction mixture was cooled with water and an ice bath. The reaction mixture was stirred at room temperature overnight. After completion of the reaction, chloroform and water were added to separate the two phases. The aqueous phase was further extracted with chloroform. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure to give 13.80 g of methyl 1-benzyl-4-piperidinecarboxylate as an orange solid (yield: 88%).

References

[1] Arkivoc, 2010, vol. 2010, # 10, p. 132 - 148
[2] Patent: WO2004/76450, 2004, A1. Location in patent: Page 43-44
[3] Synthesis, 2002, # 7, p. 911 - 915
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4324 - 4338

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