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| | Ethyl 1-benzylpiperidine-4-carboxylate Basic information | | Uses Synthesis |
| | Ethyl 1-benzylpiperidine-4-carboxylate Chemical Properties |
| Boiling point | 122°C (0.5 mmHg) | | density | 1.037 g/mL at 25 °C | | refractive index | 1.5120-1.5160 | | Fp | >110℃ | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform (Slightly), Hexanes (Slightly), Methanol (Slightly) | | pka | 7.93±0.10(Predicted) | | form | clear liquid | | color | Colorless to Light red | | InChI | InChI=1S/C15H21NO2/c1-2-18-15(17)14-8-10-16(11-9-14)12-13-6-4-3-5-7-13/h3-7,14H,2,8-12H2,1H3 | | InChIKey | ASQCOPJFYLJCGD-UHFFFAOYSA-N | | SMILES | N1(CC2=CC=CC=C2)CCC(C(OCC)=O)CC1 | | CAS DataBase Reference | 24228-40-8(CAS DataBase Reference) |
| Hazard Codes | Xi,T | | Risk Statements | 36/37/38-25 | | Safety Statements | 24/25-45 | | RIDADR | UN 2810 6.1 / PGIII | | Hazard Note | Irritant | | HS Code | 29333990 |
| | Ethyl 1-benzylpiperidine-4-carboxylate Usage And Synthesis |
| Uses | Ethyl 1-benzyl-4-piperidinecarboxylate and its derivatives are important pharmaceutical intermediates with high biological activity. Ethyl 1-benzyl-4-piperidinecarboxylate can be used to synthesize anti-inflammatory drug trypsin inhibitors, antagonizing inflammatory mediators at the receptor level. It can also be used to synthesize antitumor drugs such as matrix metalloproteinase inhibitors and farnesyltransferase inhibitors. In summary, ethyl 1-benzyl-4-piperidinecarboxylate and its derivatives possess excellent biological activity and can be used not only to synthesize GABA uptake inhibitors and antitumor drugs, but also to synthesize growth hormone secretagogues, anti-inflammatory and analgesic drugs, cardiovascular drugs, nootropic drugs, antiviral drugs, and bone disease drugs. | | Synthesis | Ethyl isonipecotate (50 g, 0.31 mol) was dissolved in toluene (150 mL) in a round
bottom flask, charged with potassium carbonate (60 g, 0.43
mol) and stirred for 15 min. Benzyl chloride (42 g, 0.31 mol)
was charged and the reaction mass was refluxed for 4 h at
100 °C. Upon completion of the reaction as marked by TLC
(hexane:ethyl acetate; 2:1), the reaction mass was cooled to
room temperature and quenched with water (100 mL), stirred
and the organic phase was separated. The aqueous phase was
again extracted with toluene (100 mL). Combined organic
phase was washed twice with saturated brine solution (50 mL).
Remove toluene in vacuo to obtain Ethyl N-benzylpiperidine-4-carboxylate
( 6.97 g, 91 %) as a yellow liquid.
 | | Chemical Properties | Colourless Oil | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 22, p. 6938 - 6942,5
[2] Journal of medicinal chemistry, 1980, vol. 23, # 8, p. 848 - 851
[3] Patent: WO2010/12611, 2010, A1. Location in patent: Page/Page column 28
[4] Journal of Medicinal Chemistry, 1996, vol. 39, # 3, p. 749 - 756
[5] Organic Preparations and Procedures International, 1994, vol. 26, # 3, p. 421 - 428 |
| | Ethyl 1-benzylpiperidine-4-carboxylate Preparation Products And Raw materials |
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