1-[(Benzyloxy)carbonyl]piperidine-4-carboxylic acid Chemical Properties

Melting point:

78 °C

Boiling point:

443.9±45.0 °C(Predicted)

Density 

1.265±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.55±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C14H17NO4/c16-13(17)12-6-8-15(9-7-12)14(18)19-10-11-4-2-1-3-5-11/h1-5,12H,6-10H2,(H,16,17)

InChIKey

URTPNQRAHXRPMP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

10314-98-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36/37/39-37/39

HazardClass 

IRRITANT

HS Code 

29333990

1-[(Benzyloxy)carbonyl]piperidine-4-carboxylic acid Usage And Synthesis

Chemical Properties

Whtie powder

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 42, p. 147, 1994 DOI: 10.1248/cpb.42.147

Synthesis

NaHCO3 (1.5 eq.) and Na2CO3 (1.5 eq.) were added to 4-piperidinecarboxylic acid (1.29 g, 10 mmol) in a mixed solvent of acetonitrile/water (2:3, 0.1 M) and the pH was adjusted to 10-11. The reaction mixture was cooled down to 0 °C and then benzyl chloroformate (1.42 mL, 1.7 g, 10 mmol) was slowly added dropwise. After the dropwise addition, the reaction solution was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction mixture was acidified to pH ~2-3 by dropwise addition of aqueous 1N HCl. Subsequently, acetonitrile was removed by evaporation under reduced pressure, and the aqueous phase was extracted with ethyl acetate (3 x 30 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid in quantitative yield, and the product was used directly in the next step of the reaction.

References

[1] Synlett, 2017, vol. 28, # 3, p. 376 - 380
[2] Tetrahedron, 1997, vol. 53, # 32, p. 10983 - 10992
[3] Patent: US2010/152158, 2010, A1. Location in patent: Page/Page column 31
[4] Patent: US2010/173889, 2010, A1. Location in patent: Page/Page column 60
[5] Patent: US2010/222324, 2010, A1. Location in patent: Page/Page column 57

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