ChemicalBook CAS DataBase List N-Benzyl-4-piperidone

N-Benzyl-4-piperidone synthesis

13synthesis methods

Product Name:N-Benzyl-4-piperidone
CAS Number:3612-20-2
Molecular formula:C12H15NO
Molecular Weight:189.25

41979-39-9 Synthesis

41979-39-9
117 suppliers
$15.00/10mg

100-39-0
419 suppliers
$10.00/10g

3612-20-2
499 suppliers
$6.00/10g

Yield:3612-20-2 89.28%

Reaction Conditions:

Stage #1: 4-piperidone hydrochloridewith potassium carbonate in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2: benzyl bromide in N,N-dimethyl-formamide at 65; for 14 h;

Steps:

25

A mixture of 4-piperidone monohydrate hydrochloride (2.5 g, 14.56 mmol) and anhydrous potassium carbonate (7 g, 50.64 mmol) in dry DMF (25 mL) was stirred for 30 min at room temperature. Benzyl bromide (2 mL, 16.82 mmol) was added dropwise into the reaction mixture and heated at 65 °C for 14 h. The reaction mixture was cooled to room temperature, filtered and quenched with ice water (25 mL). The resulting mixture was extracted in ethyl acetate (2 x 20 mL) and the combined organic layers were washed with water (2 x 15 mL) followed by brine (20 mL). The organic phase obtained was dried over anhydrous sodium sulphate and evaporated. The crude product obtained was purified by crystallisation using 2 % methanol in chloroform to afford the title compound.Yield: 2.5 g (89.28 %); ¹ HNMR (CDCI₃, 300MHz): δ 7.34 (m, 4H), 7.29 (m, 1 H), 3.62 (S, 2H), 2.75 (t, 4H), 2.46 (t, 4H).

References:

WO2011/104680,2011,A1 Location in patent:Page/Page column 77-78

793-19-1 Synthesis