1-BENZYLPIPERIDINE-3-CARBOXYLIC ACID

1-BENZYLPIPERIDINE-3-CARBOXYLIC ACID Property

Boiling point:

358.6±35.0 °C(Predicted)

Density 

1.165

storage temp. 

Sealed in dry,Room Temperature

pka

3.85±0.20(Predicted)

Appearance

White to off-white Solid

Safety

Hazard Codes 

Xn

Risk Statements 

22

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P363Wash contaminated clothing before reuse.

P403Store in a well-ventilated place.

1-BENZYLPIPERIDINE-3-CARBOXYLIC ACID Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 1-benzylpiperidine-3-carboxylic acid from ethyl 1-benzylpiperidine-3-carboxylate was as follows: a 4N aqueous sodium hydroxide solution (15 ml) was slowly added to a mixture of tetrahydrofuran (30 ml) and 1,4-dioxane (30 ml) containing ethyl 1-benzyl-3-piperidinecarboxylate (7.00 g, 28.3 mmol). The reaction mixture was stirred at room temperature for 4 hours. Subsequently, 4N aqueous sodium hydroxide solution (15 ml) was added again and stirring was continued at room temperature overnight. After completion of the reaction, 2N hydrochloric acid (15 ml) was slowly added to neutralize the reaction solution under ice bath cooling conditions. The neutralized mixture was azeotropically dehydrated using toluene. The obtained residue was suspended in ethanol and after filtration, the filtrate was concentrated to finally obtain 1-benzyl-3-piperidine carboxylic acid (6.3 g, 100% yield).

References

[1] Patent: EP1403255, 2004, A1. Location in patent: Page 66
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5512 - 5532
[3] Patent: WO2008/55959, 2008, A1. Location in patent: Page/Page column 65