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194352

Sigma-Aldrich

Ethyl 1-methyl-3-piperidinecarboxylate

96%

Synonym(s):

1-Methyl-nipecotic acid ethyl ester, Ethyl 1-methylnipecotate, NSC 64739

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About This Item

Empirical Formula (Hill Notation):
C9H17NO2
CAS Number:
5166-67-6
Molecular Weight:
171.24
Beilstein/REAXYS Number:
123259
EC Number:
225-951-0
MDL number:
MFCD00006496
UNSPSC Code:
12352100
PubChem Substance ID:
24851646
NACRES:
NA.22

assay

96%

refractive index

n20/D 1.451 (lit.)

bp

88-89 °C/11 mmHg (lit.)

density

0.954 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C1CCCN(C)C1

InChI

1S/C9H17NO2/c1-3-12-9(11)8-5-4-6-10(2)7-8/h8H,3-7H2,1-2H3

InChI key

VFJJNMLPRDRTCO-UHFFFAOYSA-N

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General description

Enantiomeric discrimination has been investigated in 1H and 13C NMR spectra of ethyl 1-methyl-3-piperidinecarboxylate in the presence of (-)-(18-crown-6)-2,3,11,12-tetracarboxylic acid.

Application

Reactant for:
N-demethylation of tertiary amines
Reverse cope elimination reactions
Regioselective oxidation
Synthesis of chelating agents
Sequential Michael-Michael-Dieckmann cyclizations

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

154.4 °F - closed cup

flash_point_c

68 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
01611CJ
05503AH
07113AS

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Ming-Hsui Tsai et al.
Psychiatry research, 271, 153-160 (2018-11-27)
The purposes of this study were to develop the Chinese-version betel quid dependence instrument (BQDI) and to test its reliability and validity. An item pool relevant to betel quid dependence was generated. A panel of three experts assessed content validity
Ann E Lovely et al.
The Journal of organic chemistry, 71(24), 9178-9182 (2006-11-18)
Enantiomeric discrimination is observed in the (1)H and (13)C NMR spectra of piperidines and piperazines in the presence of (-)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. The amines are protonated by the carboxylic acid groups of the crown ether to produce the corresponding ammonium and

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