4-AMINO-1-BENZYL-PIPERIDINE-4-CARBOXYLIC ACID Chemical Properties

Melting point:

247-248°

Boiling point:

385.7±42.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

1.73±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C13H18N2O2/c14-13(12(16)17)6-8-15(9-7-13)10-11-4-2-1-3-5-11/h1-5H,6-10,14H2,(H,16,17)

InChIKey

UAPJXCZSNCQLMR-UHFFFAOYSA-N

SMILES

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

Safety Information

Risk Statements 

36

Safety Statements 

26

HS Code 

2933399990

4-AMINO-1-BENZYL-PIPERIDINE-4-CARBOXYLIC ACID Usage And Synthesis

Synthesis

The general procedure for the synthesis of 1-benzyl-4-amino-4-piperidinecarboxylic acid using 8-benzyl-2,4-dioxo-1,3,8-triazaspiro[4,5]decane as a starting material was as follows: 2.4 kg of sodium hydroxide was dissolved in 10 L of deionized water in a 20 L reactor. Subsequently, 614 g of 8-benzyl-1,3,8-triazaspiro[4.5]decane-2,4-dione (1.38) was added to this solution to form a reaction suspension. The suspension was heated to 80°C. After reaching 80°C, the temperature was gradually increased at a rate of 10°C per step. When the temperature was raised to 105°C, the reaction mixture began to foam vigorously. The reaction was maintained at 108°C with continuous stirring overnight. Upon completion of the reaction, the mixture was cooled to 10 °C, and 5 L of concentrated hydrochloric acid was slowly added dropwise to adjust the pH to 7-8. During the dropwise addition, the reaction temperature was controlled to be no more than 23 °C. A solid was precipitated from the reaction solution and the precipitate was collected by filtration. The resulting solid was dried under vacuum at 40 °C for 3 days, followed by drying at 80 °C overnight to give 469.7 g of 1-benzyl-4-amino-4-piperidinecarboxylic acid (I.39) in a final yield of 85% of the theoretical value.

References

[1] Patent: WO2012/101013, 2012, A1. Location in patent: Page/Page column 97; 98
[2] Patent: US2013/23502, 2013, A1. Location in patent: Paragraph 0266; 0269-0270
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3972 - 3983
[4] Patent: WO2016/78771, 2016, A1. Location in patent: Page/Page column 134

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