1-METHYL-PIPERIDINE-4-CARBOXYLIC ACID Chemical Properties

Boiling point:

246.1±33.0 °C(Predicted)

Density 

1.103

refractive index 

1.488

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

3.16±0.20(Predicted)

color 

Pale yellow

InChI

InChI=1S/C7H13NO2/c1-8-4-2-6(3-5-8)7(9)10/h6H,2-5H2,1H3,(H,9,10)

InChIKey

HCKNAJXCHMACDN-UHFFFAOYSA-N

SMILES

N1(C)CCC(C(O)=O)CC1

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

29333990

1-METHYL-PIPERIDINE-4-CARBOXYLIC ACID Usage And Synthesis

Uses

1-Methylpiperidine-4-carboxylic acid is a heterocyclic organic compound and can be used as a pharmaceutical intermediate.

Chemical Properties

White solid

Synthesis

Using 4-piperidinecarboxylic acid (1 kg, 7.74 mol) and formaldehyde (37% aqueous solution, 720 g, 8.87 mol, 1.15 eq.) as feedstock, a wet Pd/C catalyst (10%; 55% paste, 100 g) was added to 10 L of water and the mixture was transferred to a stainless steel hydrogenation reactor. The reactor was pressurized with hydrogen (3 bar) and the reaction mixture was reacted overnight at 16-25 °C with a stirring speed of 200-2500 rpm. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was washed with 500 mL of water and subsequently concentrated under vacuum. The residue was azeotropically distilled by ethanol (2 x 1 L) to remove residual water. Finally, the resulting solid was dried under vacuum at 50 °C overnight to afford 1-methylpiperidine-4-carboxylic acid as an off-white solid (1087 g, 98.1% yield).

References

[1] Patent: WO2003/84949, 2003, A1. Location in patent: Page/Page column 45; 46
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10118 - 10129
[3] Patent: US6777428, 2004, B1. Location in patent: Page column 24
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 4, p. 449 - 459
[5] Patent: WO2008/62182, 2008, A1. Location in patent: Page/Page column 161-162

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