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380253

Sigma-Aldrich

Ethyl pipecolinate hydrochloride

97%

Synonym(s):

Ethyl 2-piperidinecarboxylate hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C8H15NO2 · HCl
CAS Number:
77034-33-4
Molecular Weight:
193.67
MDL number:
MFCD00134518
UNSPSC Code:
12352100
PubChem Substance ID:
24863731
NACRES:
NA.22

assay

97%

mp

211-213 °C (lit.)

SMILES string

Cl[H].CCOC(=O)C1CCCCN1

InChI

1S/C8H15NO2.ClH/c1-2-11-8(10)7-5-3-4-6-9-7;/h7,9H,2-6H2,1H3;1H

InChI key

KGAWPIXNSIYQPC-UHFFFAOYSA-N

General description

Ethyl pipecolinate hydrochloride is a heterocyclic building block. It is reported to participate in the total synthesis of the (+)-epiquinamide, a quinolizidine alkaloid.[1]

Application

Ethyl pipecolinate hydrochloride (Ethyl 2-piperidinecarboxylate hydrochloride) may be used in the preparation of:
  • 1,4-diazabicyclo[4.4.0]decane[2]
  • small molecule inhibitors of Legionella MIP protein[3]
  • antiinflammatory and analgesic molecules[4]
  • anti-amnesic agents[5]

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
01809LY
01224MR
01026EI
10326DF
02030DY

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Christina Juli et al.
Journal of medicinal chemistry, 54(1), 277-283 (2010-12-15)
The macrophage infectivity potentiator (MIP) protein is a major virulence factor of Legionella pneumophila, the causative agent of Legionnaires' disease. MIP belongs to the FK506-binding proteins (FKBP) and is necessary for optimal intracellular survival and lung tissue dissemination of L.
A concise synthesis of (?) and a total synthesis of (+)-epiquinamide.
Tong STA and Barker D.
Tetrahedron Letters, 47(29), 5017-5020 (2006)
G. A. Gevorgyan, et al.,
Khim.-Farm. Zh., 37, 152-154 (2003)
Syntheses of 1, 4-Diazabicyclo [4.4. 0] decanes, 1, 4-Diazabicyclo [4.3. 0] nonanes and 1, 8-Diazabicyclo [4.3. 0] nonanes.
Freed ME and Day AR.
J. Org. React., 25(12), 2108-2113 (1960)
S Zhao et al.
Bioorganic & medicinal chemistry, 7(8), 1637-1646 (1999-09-11)
Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine have been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research was undertaken to

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