4-CARBOXYMETHOXY-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER Chemical Properties

Boiling point:

390.4±42.0 °C(Predicted)

Density 

1.187±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-2.34±0.40(Predicted)

Appearance

Colorless to light yellow Solid-liquid mixture

InChI

InChI=1S/C15H19NO4/c1-19-14(17)13-7-9-16(10-8-13)15(18)20-11-12-5-3-2-4-6-12/h2-6,13H,7-11H2,1H3

InChIKey

SLMXUTJFULFSMQ-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

4-CARBOXYMETHOXY-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl N-Cbz-4-piperidinecarboxylate from methanol and 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid: concentrated sulfuric acid (two drops, using a Pasteur pipette) was slowly added dropwise (two drops) to a methanolic solution of 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid (540 mg, 2.05 mmol), and the reaction mixture was heated and refluxed for 5 hours. Upon completion of the reaction, the solution was cooled to room temperature and subsequently concentrated under reduced pressure. To the concentrated residue was added saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated under reduced pressure to afford methyl N-Cbz-4-piperidinecarboxylate (532 mg, 1.92 mmol, 93% yield) as a colorless oil.1H-NMR (400 MHz, CDCl3) δ: 1.57-1.73 (2H, m), 1.82-1.96 (2H, m), 2.43-2.55 ( 1H, m), 2.85-2.97 (2H, m), 3.69 (3H, s), 4.02-4.17 (2H, m), 5.12 (2H, s), 7.29-7.40 (5H, m).IR (neat, cm-1): 1732, 1696, 1450, 1433, 1223, 1192, 1175, 1040.

References

[1] Patent: EP2009006, 2008, A1. Location in patent: Page/Page column 81-82
[2] Patent: US2010/152158, 2010, A1. Location in patent: Page/Page column 31
[3] Patent: US2010/173889, 2010, A1. Location in patent: Page/Page column 60
[4] Patent: US2010/222324, 2010, A1. Location in patent: Page/Page column 57
[5] Patent: US2010/234340, 2010, A1. Location in patent: Page/Page column 41

4-CARBOXYMETHOXY-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER(138163-07-2)Related Product Information

• 1-Cbz-4-Piperidone
• tert-butyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylate
• N-Boc-Piperidine-4-carboxylic acid methyl ester
• Ethyl N-Boc-piperidine-4-carboxylate
• ETHYL 1-BENZYLPIPERIDINE-3-CARBOXYLATE
• ETHYL 1-CBZ-PIPERIDINE-2-CARBOXYLATE
• Ethyl 1-methylnipecotate
• Ethyl 1-methyl-4-piperidinecarboxylate
• Methyl N-methyl piperidine-4-carboxylate
• Ethyl 1-methylpipecolinate
• METHYL 1-BENZYLPIPERIDINE-4-CARBOXYLATE
• Ethyl 1-benzylpiperidine-4-carboxylate
• Benzyl 2-methylpiperidine-1,2-dicarboxylate
• 1-[(Benzyloxy)carbonyl]piperidine-4-carboxylic acid
• Methyl 1-methylpiperidine-3-carboxylate
• 1-BENZYL 4-ETHYL PIPERIDINE-1,4-DICARBOXYLATE
• 4-CARBOXYMETHOXY-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER
• 3-CARBOXYMETHOXY-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER