Benzyl 4-hydroxy-1-piperidinecarboxylate Chemical Properties

Boiling point:

167 °C/0.2 mmHg (lit.)

Density 

1.554 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.543(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Oil

pka

14.79±0.20(Predicted)

color 

Orange

InChI

InChI=1S/C13H17NO3/c15-12-6-8-14(9-7-12)13(16)17-10-11-4-2-1-3-5-11/h1-5,12,15H,6-10H2

InChIKey

JKIUUDJOCYHIGY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

95798-23-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich

Benzyl 4-hydroxy-1-piperidinecarboxylate Usage And Synthesis

Uses

Reactant for synthesis of:
Orally bioavailable P2Y12 antagonists for inhibition of platelet aggregation
Piperidine derivatives
Molecular rods
Oxazolidinone-quinolone hybrids and their antibacterial activity
Cyclic prodrug of RGD peptidomimetic

Reactant for oxidation of alcohols

Synthesis

General procedure for the synthesis of N-Benzyloxycarbonyl-4-hydroxypiperidine from 4-hydroxypiperidine and benzyl chloroformate: over 30 min, benzyl chloroformate (8.55 mL; 60 mmol) was slowly added dropwise to a well-stirred 4-hydroxypiperidine (5 g; 49.44 mmol), a 1N aqueous NaOH solution (60 mL; 60 mmol) and dioxane (60 mL) in a in a cooled mixture. After dropwise addition, the reaction mixture was continued to stir for 30 minutes. Upon completion of the reaction, the reaction mixture was treated with water and subsequently concentrated and acidified with hydrochloric acid to pH 2. The acidified aqueous phase was extracted with EtOAc, the organic phases were combined, washed with water and saturated brine in that order, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by fast column chromatography (silica gel was the stationary phase, and the eluents were petroleum ether with 50% dichloromethane (60-80 °C) and 10% acetonitrile containing 2% methanol in chloroform solution). The final product was 12.5 g (99% yield) of N-Cbz-4-hydroxypiperidine as an oil; mass spectrum (chemical ionization): m/z 236 (M++1), 218, 192, 174, 91.

References

[1] Patent: WO2005/35495, 2005, A2. Location in patent: Page/Page column 129
[2] Patent: US7759387, 2010, B2. Location in patent: Page/Page column 113
[3] Bioorganic Chemistry, 2002, vol. 30, # 4, p. 285 - 301
[4] Chemistry - A European Journal, 2007, vol. 13, # 17, p. 4859 - 4872
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 12, p. 3236 - 3240

Benzyl 4-hydroxy-1-piperidinecarboxylate(95798-23-5)Related Product Information

• Benzyl benzoate
• 4-Nitrobenzyl chloroformate
• Benzyl acetate
• Benzyl chloride
• Benzyl formate
• Benzyl chloroformate
• CHLOROPHOSPHONAZO III
• Benzyl alcohol
• Benzoyl peroxide
• Azido-PEG1-CH2CO2H
• 4-HYDROXY-3-METHYLBENZOIC ACID
• Hexahydroisonicotinamide
• 4-Pyrimidinecarboxylic acid
• Isonipecotic acid
• 4,4-Piperidinediol hydrochloride
• Benzyl
• 4-Hydroxypiperidine
• trans-3,4-Dihydroxypiperidine-1-carboxylic acid benzyl ester