ChemicalBook CAS DataBase List 1-Methyl-4-piperidinemethanol

1-Methyl-4-piperidinemethanol synthesis

7synthesis methods

Product Name:1-Methyl-4-piperidinemethanol
CAS Number:20691-89-8
Molecular formula:C7H15NO
Molecular Weight:129.2

123855-51-6 Synthesis

123855-51-6
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$6.00/5g

20691-89-8
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$6.00/1g

Yield:20691-89-8 88%

Reaction Conditions:

Stage #1: tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylatewith lithium aluminium tetrahydride in tetrahydrofuran at 20;Inert atmosphere;
Stage #2: with water;sodium hydroxide in tetrahydrofuran at 0 - 20;

Steps:

1 (1-Methylpiperidin-4-yl)methyl 4-nitrophenyl carbonate

A solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (1.94 g, 9.0 mmol) in THF (15.0 mL) was added drop-wise to a 1M solution of LiAlH₄ in THF (13.5 mL, 13.5 mmol) under argon. The reaction mixture was stirred at room temperature for 17 hours and then cooled to 0° C. A mixture of THF and water (1:1 ratio, 1.5 mL) was added drop-wise. A gelatinous white solid formed. 4M aq NaOH solution (0.6 mL) was added drop-wise. Water (2 mL) was added and the resulting mixture stirred at room temperature for 2 hours. The white solid was removed by filtration. The filtrate was loaded onto an Isolute HM-N liquid-liquid extraction column and then eluted with EtOAc (200 mL). The resulting organic phase concentrated in vacuo yielding (1-methylpiperidin-4-yl)methanol as a yellow oil (1.02 g, 88%). Analytical LCMS: purity ~90% (System B, R_T=1.88 min), ES⁺: 129.8 [MH]⁺. (

References:

US2009/281087,2009,A1 Location in patent:Page/Page column 9-10

24252-37-7 Synthesis