| Identification | More | [Name]
Methyl isonipecotate | [CAS]
2971-79-1 | [Synonyms]
4-PIPERDINECARBOXYLIC ACID, METHYL ESTER
4-PIPERIDINECARBOXYLIC ACID METHYL ESTER
ISONIPECOTIC ACID, METHYL AND ETHYL ESTERS
METHYL 4-PIPERIDINECARBOXYLATE
METHYL ISONIPECOTATE
METHYL PIPERIDINE-4-CARBOXYLATE
piperidine-4-carboxylicacidmethylester
Isonipecotic acid methyl ester
Methyl Piperidinecarboxylate
Ethyl nipecotate hydrochloride(Ethyl 3-Piperidinecarboxylate hydrochloride)
Methyl Isonipecotate hydrochloride
(Methyl 4-Piperidinecarboxylate hydrochloride)
Methyl Isonipecotate(Methyl Piperidinecarboxylate)
Methyl isonipecotate, technical grade
Methyl-4-Piperridinecarboxylate
4-PIPERIDINECARBOXYLIC ACID METHYL ESTER 99%
4-(Methoxycarbonyl)piperidine
Methyl isonipecotinate
Isonipecotic acid methyl | [EINECS(EC#)]
629-683-9 | [Molecular Formula]
C7H13NO2 | [MDL Number]
MFCD00190578 | [Molecular Weight]
143.18 | [MOL File]
2971-79-1.mol |
| Chemical Properties | Back Directory | [Boiling point ]
85-90 °C (lit.) | [density ]
1.06 | [refractive index ]
1.465 | [Fp ]
192°F | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [solubility ]
Chloroform | [form ]
Liquid | [pka]
9.78±0.10(Predicted) | [color ]
Colorless to yellow | [Water Solubility ]
Slightly soluble in water. | [CAS DataBase Reference]
2971-79-1(CAS DataBase Reference) |
| 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:Wear suitable protective clothing . | [RIDADR ]
3267 | [WGK Germany ]
3 | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
4-Piperidinecarboxylic acid methyl ester is a an ester derivative of 4-piperidinecarboxylic acid used as a reagent in the organic synthesis of neurochemicals, antibacterials and other biologically active compounds.
| [General Description]
Methyl isonipecotate can be obtained by the reduction of methyl isonicotinate in methanol with ruthenium at 100-150°C. | [Synthesis]
The general procedure for the synthesis of methyl 4-piperidinecarboxylate from the compound (CAS: 1262670-73-4) is as follows: the substrate (1 eq.) was dissolved in a minimal amount of water (about 15 eq.) containing CAN (20 mol%). The reaction mixture was transferred to dichloromethane and magnetically stirred. Acetic acid (10 equivalents) was added to the solution, followed by stirring at room temperature for the time specified in Table 2. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure and post-treated as follows. Method A: The solid residue was washed twice with petroleum ether to remove the by-product triphenylmethanol. Subsequently, the residue was dissolved in methanol and filtered through a short diatomaceous earth pad. The solvent was removed by evaporation under reduced pressure to obtain the free amine. Method B: Water and acetic acid were removed from the reaction mixture under vacuum. The residue was dissolved in anhydrous dichloromethane, followed by the addition of triethylamine (2.5 eq.) and acetic anhydride or benzoyl chloride (1.5 eq.). After completion of the reaction, the solvent was removed by evaporation. The residue was extracted twice with ethyl acetate. The organic layers were combined, washed sequentially with water and brine and finally dried over Na2SO4. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography to afford the acylated amine. | [References]
[1] Tetrahedron Letters, 2011, vol. 52, # 1, p. 34 - 37 |
|
|