| Identification | More | [Name]
Ethyl 1-methylnipecotate | [CAS]
5166-67-6 | [Synonyms]
1-METHYL-PIPERIDINE-3-CARBOXYLIC ACID ETHYL ESTER
ETHYL 1-METHYL-3-PIPERIDINE-CARBOXYLATE
ETHYL 1-METHYLNIPECOTATE
ETHYL 1-METHYLPIPERIDINE-3-CARBOXYLATE
LABOTEST-BB LT00159658
3-Piperidinecarboxylic acid, 1-methyl-, ethyl ester
Ethyl 1-methylpiperidine-3-carboxylate 97%
Ethyl 1-methylnipecotate, 98+%
1-Methyl-3-piperidinecarboxylic acid ethyl ester | [EINECS(EC#)]
225-951-0 | [Molecular Formula]
C9H17NO2 | [MDL Number]
MFCD00006496 | [Molecular Weight]
171.24 | [MOL File]
5166-67-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to pale yellow liquid | [Boiling point ]
88-89 °C/11 mmHg (lit.) | [density ]
0.954 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.451(lit.)
| [Fp ]
155 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
clear liquid | [pka]
8.56±0.10(Predicted) | [color ]
Colorless to Almost colorless | [BRN ]
123259 | [InChI]
1S/C9H17NO2/c1-3-12-9(11)8-5-4-6-10(2)7-8/h8H,3-7H2,1-2H3 | [InChIKey]
VFJJNMLPRDRTCO-UHFFFAOYSA-N | [SMILES]
CCOC(=O)C1CCCN(C)C1 | [CAS DataBase Reference]
5166-67-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethyl 1-methylnipecotate(5166-67-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [F ]
9-23 | [Hazard Note ]
Irritant | [HS Code ]
29333990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to pale yellow liquid | [Uses]
Reactant for:
N-demethylation of tertiary amines
Reverse cope elimination reactions
Regioselective oxidation
Synthesis of chelating agents
Sequential Michael-Michael-Dieckmann cyclizations | [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. | [Synthesis]
The general procedure for the synthesis of ethyl 1-methyl-3-piperidinecarboxylate from triethyl orthoformate and ethyl crotonate is as follows: in an autoclave, a 1 molar concentration of catalyst based on the molar amount of amine is added, and after displacing the air in the autoclave with argon, 0.1 moles of amine and 0.11-0.3 moles of o-carboxylic acid ester dissolved in a 10 ml solution in methanol (or ethanol) are added, as well as 0.5 ml of 0.2 M anhydrous p-toluene benzenesulfonic acid solution in methanol (or ethanol). The reaction mixture was heated to 120°C and charged with hydrogen gas to a pressure of 40 bar. The reaction mixture was stirred continuously at a constant pressure until the absorption of hydrogen ceased (reaction time of about 0.2-6 hours). After completion of the reaction, the catalyst was removed by filtration and the filtrate was distilled to purify the target product. | [References]
[1] Patent: WO2017/133913, 2017, A1. Location in patent: Page/Page column 9; 14 |
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