ChemicalBook CAS DataBase List 4-PIPERIDIN-1-YL-BENZALDEHYDE

4-PIPERIDIN-1-YL-BENZALDEHYDE synthesis

8synthesis methods

Product Name:4-PIPERIDIN-1-YL-BENZALDEHYDE
CAS Number:10338-57-5
Molecular formula:C12H15NO
Molecular Weight:189.25

110-89-4

459-57-4

10338-57-5

General procedure for the synthesis of 4-piperidin-1-yl-benzaldehyde from hexahydropyridine and p-fluorobenzaldehyde: A mixture of p-fluorobenzaldehyde (25.0 g, 0.200 mol), hexahydropyridine (0.300 mol), and anhydrous potassium carbonate (40.0 g) was mixed in DMF (300 mL) and a catalytic amount of Aliquat 336 reagent was added. The reaction mixture was refluxed at 100 °C for 24 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure and cooled to room temperature. Subsequently, the mixture was poured into ice water and allowed to stand overnight. The solid product formed was filtered, washed with water and recrystallized with methanol to afford the target compound 4-(piperidin-1-yl)benzaldehyde. The compound was obtained in 98% yield as yellow crystals with a melting point of 64°C, which is in agreement with literature reports [47,48].

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Yield: 92%

Reaction Conditions:

with water;sodium t-butanolate in toluene at 105; for 4 h;Schlenk technique;

Steps:

Palladium-catalyzed amination of aryl bromides
General procedure: An oven-dried Schlenk tube was charged with the aryl halide (2 mmol) and amine (2.5 mmol), FeOA-Pd (0.05 g, 0.04 mmol, 1.5 mol%), base (3 mmol), solvent (5 mL) and additive. The resulting mixture was stirred for the appropriate time and temperature. After reaction completion the reaction mixture was then cooled to room temperature and the catalyst separated using a magnet, taken up in Et₂O (4 mL), and washed with brine (5 mL). The resulting solution was dried over anhydrous MgSO₄, filtered and concentrated. The crude product was purified by flash chromatography on silica gel.

References:

Rafiee, Ezzat;Ataei, Ali;Joshaghani, Mohammad [Tetrahedron Letters,2016,vol. 57,# 2,p. 219 - 222]

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104-88-1 Synthesis