ChemicalBook CAS DataBase List 4-Piperidinemethanol

4-Piperidinemethanol synthesis

14synthesis methods

Product Name:4-Piperidinemethanol
CAS Number:6457-49-4
Molecular formula:C6H13NO
Molecular Weight:115.17

1126-09-6

6457-49-4

The general procedure for the synthesis of 4-hydroxymethylpiperidine from ethyl 4-piperidinecarboxylate was as follows: lithium aluminum hydride (LiAlH4, 10.10 g, 0.266 mol) was suspended in tetrahydrofuran (THF, 150 mL) at 0 °C. Subsequently, a solution of ethyl 4-piperidinecarboxylate (18.13 g, 0.120 mol) dissolved in THF (300 mL) was slowly added. The reaction mixture was stirred at room temperature overnight. After the reaction was completed, it was cooled in an ice bath and a mixture of water (14 mL) and THF (28 mL) was slowly added. Next, a mixture of 15% aqueous sodium hydroxide (14 mL) and water (37 mL) was added and stirring was continued for 30 minutes at room temperature. The reaction mixture was filtered to remove the precipitate and the filtrate was concentrated to give 17.88 g of the target product 4-hydroxymethylpiperidine in quantitative yield.

1126-09-6 Synthesis

1126-09-6
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$15.40/25g

6457-49-4
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$18.00/25g

Yield:6457-49-4 100%

Reaction Conditions:

Stage #1: 4-carbethoxypiperidinewith lithium aluminium tetrahydride in tetrahydrofuran at 20;
Stage #2: with sodium hydroxide;water in tetrahydrofuran at 20; for 0.5 h;

Steps:

28.a; 29.a EXAMPLE 28; 2-[1-(tert-Butoxycarbonyl)piperidin-4-ylmethyl]-4, 6-bis (4-FLUOROPHENYL)-5-(4- PYRIDYL) PYRAZOLO [3, 4-B] PYRIDINE; EXAMPLE 29; 1- [1- (TERT BUTOXYCARBONYL) PIPERIDIN-4-YLMETHYL]-4, 6-BIS (4-FLUOROPHENYL)-5- (4- PYRIDYL) PYRAZOLOL3, 4-B] PYRIDINE; A) (4-PIPERIDYL) METHANOL

To A suspension of LIAIH4 (10. 10 G, 0. 266 MOL) IN THF (150 ML) AT 0 C, A SOLUTION OF ETHYL PIPERIDINE-4-CARBOXYLATE (18. 13 G, 0. 120 MOL) IN THF (300 ML) WAS ADDED slowly. This was stirred at room temperature overnight. It was cooled with an ice bath and A mixture of water (14 ML) and THF (28 ML) was added slowly. Afterwards, A mixture of 15% aqueous NAOH (14 mL) and water (37 ML) was added followed by stirring at room temperature for 30 min. The precipitate obtained was filtered and the filtrate was concentrated, to afford 17. 88 g of the desired compound (yield : quantitative).

References:

WO2004/76450,2004,A1 Location in patent:Page 59

498-94-2 Synthesis