| Identification | More | [Name]
Ethyl 4-piperidinecarboxylate | [CAS]
1126-09-6 | [Synonyms]
4-PIPERDINECARBOXYLIC ACID, ETHYL ESTER
4-PIPERIDINECARBOXYLIC ACID ETHYL ESTER
AKOS MSC-0737
ETHYL 4-PIPERIDINECARBOXYLATE
ETHYL ISONIPECOTATE
ETHYL PIPERIDINE-4-CARBOXYLATE
ISONIPECOTIC ACID ETHYL ESTER
ISONIPECOTINIC ACID ETHYL ESTER
LABOTEST-BB LT00159543
PIPERIDINE-4-CARBOXYLIC ACID ETHYL ESTER
RARECHEM AH CK 0180
TIMTEC-BB SBB004006
4-Carbethoxypiperidine
H-DL-Inp-OEt
Ethyl Isonipecotate(ethyl 4-Piperidinecarboxylate)
Hexahydroisonicotinic acid, ethyl ester
Ethyl isonipecotate, 98+%
Ethyl piperidine-4-carboxylate 97%
ethylpiperidine-2-carboxylate（hydrochloride
Ethyl 4-Piperidinecarboxylate (Ethyl isonipecotate) | [EINECS(EC#)]
214-416-7 | [Molecular Formula]
C8H15NO2 | [MDL Number]
MFCD00006003 | [Molecular Weight]
157.21 | [MOL File]
1126-09-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to slightly brown liquid | [Boiling point ]
204 °C(lit.)
| [density ]
1.02 g/mL at 25 °C(lit.)
| [vapor pressure ]
39.4Pa at 25℃ | [refractive index ]
n20/D 1.459(lit.)
| [Fp ]
176 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Liquid | [pka]
9.83±0.10(Predicted) | [color ]
Clear colorless to slightly brown | [Water Solubility ]
miscible | [Detection Methods]
HPLC,GC,NMR | [BRN ]
118419 | [InChI]
InChI=1S/C8H15NO2/c1-2-11-8(10)7-3-5-9-6-4-7/h7,9H,2-6H2,1H3 | [InChIKey]
RUJPPJYDHHAEEK-UHFFFAOYSA-N | [SMILES]
N1CCC(C(OCC)=O)CC1 | [LogP]
1.15 | [CAS DataBase Reference]
1126-09-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethyl piperidine-4-carboxylate(1126-09-6) |
| Safety Data | Back Directory | [Hazard Codes ]
C,Xi | [Risk Statements ]
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN2735 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29333999 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to slightly brown liquid | [Uses]
Reactant for synthesis of SMN protein modulators and β-aryl and β-amino-substituted aliphatic esters by rhodium catalyzed tandem double bond migration/conjugate addition. | [Uses]
Reactant for synthesis of:• ;SMN protein modulators1• ;β-aryl and β-amino-substituted aliphatic esters by rhodium catalyzed tandem double bond migration/conjugate addition2• ;Nitroethylenediamines by nucleophilic ring opening of nitroimidazolidinone3• ;RhoA inhibitors for cardiovascular disease therapy4• ;Saccharin derived Mannich bases as antimicrobials and antioxidants5Reactant for one-pot reductive amination and Suzuki-Miyaura cross coupling of formyl aryl and heteroaryl MIDA boronates6 | [Synthesis Reference(s)]
Tetrahedron Letters, 23, p. 193, 1982 DOI: 10.1016/S0040-4039(00)86783-0 | [Synthesis]
1. 4-Piperidinecarboxylic acid (1.29 g, 10.0 mmol) was dissolved in anhydrous ethanol (50 mL).
2. The reaction solution was cooled to 0 °C and thionyl chloride (2.91 mL, 40.0 mmol) was added slowly and dropwise.
3. The reaction mixture was stirred and heated to reflux for 48 hours.
4. After completion of the reaction, the solvent was evaporated under reduced pressure to give a yellow oily crude product.
5. The crude product was dissolved in ethyl acetate (EtOAc) and washed with 10% sodium hydroxide (NaOH) solution.
6. The organic layer was separated, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the clarified oily product ethyl 4-piperidinecarboxylate (1.48 g, 94% yield). 7. The product was analyzed by 1H NMR.
7. The product was characterized by 1H NMR (400 MHz, CDCl3) and mass spectrometry (ESI) to confirm the correct structure. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7106 - 7109
[2] Letters in Organic Chemistry, 2015, vol. 12, # 4, p. 277 - 279
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 5, p. 505
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2693 - 2698
[5] European Journal of Medicinal Chemistry, 2000, vol. 35, # 7-8, p. 699 - 706 |
|
|