1-Methyl-4-piperidinemethanol Chemical Properties

Boiling point:

108°C/10mmHg(lit.)

Density 

0.981 g/mL at 25 °C

refractive index 

1.476

Flash point:

110℃

storage temp. 

Inert atmosphere,Room Temperature

pka

14.94±0.10(Predicted)

form 

Liquid

color 

Colorless to yellow

InChI

InChI=1S/C7H15NO/c1-8-4-2-7(6-9)3-5-8/h7,9H,2-6H2,1H3

InChIKey

KJZLJGZZDNGGCA-UHFFFAOYSA-N

SMILES

N1(C)CCC(CO)CC1

CAS DataBase Reference

20691-89-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36/37/39

RIDADR 

2735

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

1-Methyl-4-piperidinemethanol Usage And Synthesis

Application

1-Methyl-4-piperidinemethanol is a common organic synthon, frequently used in the synthesis of drug molecules and bioactive molecules. The hydroxyl group in its structure can be converted into a chlorine atom by thionyl chloride. During the chlorination reaction, hydrogen chloride is produced, which combines with a tertiary amine, so the product is often an amine salt.

Chemical Properties

Colorless liquid

Synthesis

The general procedure for the synthesis of 1-methyl-4-piperidinemethanol from ethyl N-methyl-4-piperidinecarboxylate is as follows: Synthesis of Example 23 (1-methylpiperidin-4-yl)methanol (22): a solution of ethyl N-methyl-4-piperidinecarboxylate (21, 10.1 g, 59.0 mmol) in ethyl ether (Et2O, 40 mL) was slowly added dropwise to an ethyl ether suspension of lithium aluminum hydride (LiAlH4, 2.46 g, 64.9 mmol). The reaction system was cooled at 0 °C, followed by the addition of ether (200 mL). The reaction mixture was gradually warmed to room temperature and stirred continuously at this temperature for 4 hours. Upon completion of the reaction, the reaction was quenched by the slow addition of water (10 mL) and stirring was continued for 30 minutes. The resulting white precipitate was separated by filtration and washed well with ether (250 mL). After concentration under reduced pressure to remove the solvent, the oily product obtained was purified by distillation under reduced pressure (boiling point 108 °C, 14 mbar) to give the target compound 22 (6.40 g, 84% yield) as a colorless oil. -Thin layer chromatography (TLC) analysis: Rf = 0.53 (Expanding agent: dichloromethane/methanol = 5:1 with 5% triethylamine, phosphomolybdic acid color development: dark blue spots). -Nuclear magnetic resonance hydrogen spectrum (1H NMR, 300MHz, CDCl3): δ= 1.28 (dq, J = 12.2, 3.7Hz, 2H, 3-Hax, 5-Hax), 1.38-1.55 (m, 1H, 4-H), 1.68-1.79 (m, 2H, 3-Heq, 5-Heq), 1.93 (dt, J = 11.8, 2.3Hz, 2H, 2H, 4-H). 2.3 Hz, 2H, 2-Hax, 6-Hax), 2.26 (s, 3H, NMe), 2.82-2.92 (m, 2H, 2-Heq, 6-Heq), 3.12 (sbr, 1H, OH), 3.46 (d, J = 6.4 Hz, 2H, CH2OH) ppm. -Nuclear magnetic resonance carbon spectrum (13C NMR, 75.5 MHz, CDCl3): δ= 28.8 (C-3, C-5), 37.9 (C-4), 46.3 (NMe), 55.5 (C-2, C-6), 67.4 (CH2OH) ppm. -Mass spectrum (MS, 70eV, EI): m/z (%) = 129 (55) [M]+, 128 (100) [M-H]+, 112 (10) [M-OH]+, 98 (21) [M-CH2OH]+. -Molecular formula: C7H15NO (molecular weight: 129.20).

References

[1] European Journal of Organic Chemistry, 2006, # 10, p. 2314 - 2321
[2] Patent: US2009/318668, 2009, A1. Location in patent: Page/Page column 52
[3] Patent: WO2007/89149, 2007, A2. Location in patent: Page/Page column 96
[4] Journal of the American Chemical Society, 1952, vol. 74, p. 3831
[5] Patent: WO2005/95387, 2005, A1. Location in patent: Page/Page column 68

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