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ChemicalBook--->CAS DataBase List--->20691-89-8

20691-89-8

20691-89-8 Structure

20691-89-8 Structure
IdentificationMore
[Name]

1-Methyl-4-piperidinemethanol
[CAS]

20691-89-8
[Synonyms]

1-METHYL-4-PIPERIDINEMETHANOL
(1-METHYL-PIPERIDIN-4-YL)-METHANOL
4-HYDROXYMETHYL-1-METHYLPIPERIDINE
BUTTPARK 145\16-21
CHEMBRDG-BB 4002191
N-METHYL-4-PIPERIDINEMETHANOL
N-METHYL-4-HYDROXYMETHYLPIPERIDINE
1-Methylpiperidine-4-methanol
[EINECS(EC#)]

-0
[Molecular Formula]

C7H15NO
[MDL Number]

MFCD03411903
[Molecular Weight]

129.2
[MOL File]

20691-89-8.mol
Chemical PropertiesBack Directory
[Boiling point ]

108°C/10mmHg(lit.)
[density ]

0.981 g/mL at 25 °C
[Fp ]

110℃
[refractive index ]

1.476
[storage temp. ]

Inert atmosphere,Room Temperature
[form ]

Liquid
[pka]

14.94±0.10(Predicted)
[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 DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[RIDADR ]

2735
[WGK Germany ]

3
[HazardClass ]

IRRITANT
[HS Code ]

29333990
Hazard InformationBack Directory
[Chemical Properties]

Colorless liquid
[Synthesis]

Ethyl 1-methyl-4-piperidinecarboxylate

24252-37-7

1-Methyl-4-piperidinemethanol

20691-89-8

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
Spectrum DetailBack Directory
[Spectrum Detail]

1-Methyl-4-piperidinemethanol(20691-89-8)1HNMR
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