ChemicalBook CAS DataBase List (1-BENZYLPIPERIDIN-4-YLIDENE)ACETIC ACID ETHYL ESTER

(1-BENZYLPIPERIDIN-4-YLIDENE)ACETIC ACID ETHYL ESTER synthesis

9synthesis methods

Product Name:(1-BENZYLPIPERIDIN-4-YLIDENE)ACETIC ACID ETHYL ESTER
CAS Number:40110-55-2
Molecular formula:C16H21NO2
Molecular Weight:259.34

3612-20-2 Synthesis

3612-20-2
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(1-BENZYLPIPERIDIN-4-YLIDENE)ACETIC ACID ETHYL ESTER

40110-55-2
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$38.88/250mgs:

Yield: 98%

Reaction Conditions:

Stage #1:ethyl 2-(dimethoxyphosphoryl)acetate with sodium hydride in tetrahydrofuran for 0.666667 h;
Stage #2:1-phenylmethyl-4-piperidone in tetrahydrofuran at 20; for 1.33333 h;

Steps:

22a.1
Example 22a; N-(2-Amino-5-(thiophen-2-yl)phenyl)-2-(l-benzylpiperidin-4-ylidene)acetamide (205); Scheme 22; Step 1 : Ethyl 2-(l-benzylpiperidin-4-ylidene)acetate (203); [0813] To a suspension of sodium hydride (4.8 g, 121 mmol) in THF (300 rnL) was added a solution of ethyl 2-(dimethoxyphosphoryl)acetate (24.3 rnL, 121.2 mmol) in THF (60 mL) drop wise over 30 min. After complete addition the solution was stirred for 10 min then a solution of ketone 202 (15.3 g, 80.8 mmol) in THF (80 mL) was added drop wise over 20 min. After 60 min of stirring at room temperature, the reaction mixture was quenched with H2O, extracted with diethyl ether. The organic phase were washed with H2O, brine, dried over Na2SO4, filtered, and purified by column chromatography (30 to 40% AcOEt in hexane) to give title compound 203(20.4 g, 98% yield).[0814] LRMS: 259.20 (calc) 260.1 (obs).

References:

METHYLGENE INC. WO2007/118137, 2007, A1 Location in patent:Page/Page column 127-128

3612-20-2 Synthesis

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