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 

n20/D 1.479

Flash point:

190 °F

storage temp. 

2-8°C

form 

Liquid After Melting

pka

14.87±0.20(Predicted)

color 

Clear colorless to brown

Water Solubility 

MISCIBLE

Sensitive 

Hygroscopic

BRN 

103024

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 

Yes

HS Code 

29333999

MSDS

• Language:English Provider:1-Methyl-4-piperidinol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Methyl-4-piperidinol Usage And Synthesis

Chemical Properties

clear colorless to yellowish liquid after melting

Uses

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

Uses

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.

Flammability and Explosibility

Not classified

Synthesis

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.

References

[1] Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2474 - 2481
[2] Patent: US2015/336862, 2015, A1. Location in patent: Paragraph 0038; 0054
[3] Patent: US2767190, 1950,
[4] Patent: US2776293, 1950,
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 1826

N-Methyl-4-piperidinol (106-52-5)Related Product Information

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