N-Methyl-4-piperidinol #CAS106-52-5
The general procedure for the synthesis of 1-methyl-4-piperidinol from N-methyl-4-piperidone was as follows: in standard experiments, the catalyst complex 1 (6.1 mg, 10 mol%) and the hydrogenation reagent H[BAr'4]-(Et2O)2 (10.1 mg, 10 mol%) were dissolved in a 100 mL thick-walled glass reactor fitted with a TEFLON stopper and stirring bar of THF (2.0 mL). Subsequently, the substrate to be hydrogenated (0.5 mmol) was added. The reaction system was degassed by a freeze-pump-thaw cycle and then charged with hydrogen (1 or 4 atm). The reaction mixture was stirred at a set temperature (25-60 °C) until the reaction was complete. At the end of the reaction, the solvent was removed by evaporation and the residue was initially purified by passing through a silica gel column. After removal of solvent under reduced pressure, the crude product was dissolved in CDCl3 and analyzed by 1H NMR. The final product was further purified by column chromatography or preparative thin layer chromatography (TLC) using hexane/ethyl acetate (3:1, v/v) as eluent. The purified products were characterized by 1H NMR and GC-MS, and the spectral data were consistent with those reported in the literature or real samples.
Application of N-Methyl-4-piperidinol
Reactant for:• ;Optimization of Novobiocin scaffold to product antitumor agents1• ;Substitution about the rigidifying ring for histamine H4 receptor antagonist synthesis2Reactant for synthesis of:• ;CaMKII inhibitors3• ;VEGFR and FGFR kinase inhibitors4• ;Phosphoinositide-3-kinase inhibitors5• ;Protein lysine methyltransferase G9a inhibitors6
4-Hydroxy-1-methylpiperidine is used as reactant for optimization of Novobiocin scaffold to product antitumor agents, substitution about the rigidifying ring for histamine H4 receptor antagonist synthesis. It is also used as a reactant in the synthesis of CaMKII, VEGFR and FGFR kinase inhibitors and Phosphoinositide-3-kinase, Protein lysine methyltransferase G9a inhibitors.
| N-Methyl-4-piperidinol Chemical Properties |
| Melting point | 29-31 °C(lit.) |
| Boiling point | 200 °C(lit.) |
| density | 0.98 g/mL at 20 °C(lit.) |
| vapor pressure | 8.13-11Pa at 25℃ |
| refractive index | n |
| Fp | 190 °F |
| storage temp. | 2-8°C |
| pka | 14.87±0.20(Predicted) |
| form | Liquid After Melting |
| color | Clear colorless to brown |
| Water Solubility | MISCIBLE |
| Sensitive | Hygroscopic |
| BRN | 103024 |
| Henry's Law Constant | 1.3×103 mol/(m3Pa) at 25℃, Du et al. (2017) |
| InChI | 1S/C6H13NO/c1-7-4-2-6(8)3-5-7/h6,8H,2-5H2,1H3 |
| InChIKey | BAUWRHPMUVYFOD-UHFFFAOYSA-N |
| SMILES | CN1CCC(O)CC1 |
| LogP | -0.14-0.756 at 25℃ |
| CAS DataBase Reference | 106-52-5(CAS DataBase Reference) |
| NIST Chemistry Reference | 4-Hydroxy-N-methylpiperidine(106-52-5) |
| EPA Substance Registry System | 4-Piperidinol, 1-methyl- (106-52-5) |
| Safety Information |
| Hazard Codes | Xi,C |
| Risk Statements | 37/38-41-36/37/38-34 |
| Safety Statements | 26-37/39-45-36/37/39-27 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| TSCA | TSCA listed |
| HS Code | 29333999 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Eye Dam. 1 Skin Irrit. 2 STOT SE 3 |
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