ETHYL 2-[1-(4-NITROPHENYL)-4-PIPERIDINYLIDENE]ACETATE synthesis

5synthesis methods

Product Name:ETHYL 2-[1-(4-NITROPHENYL)-4-PIPERIDINYLIDENE]ACETATE
CAS Number:251310-52-8
Molecular formula:C15H18N2O4
Molecular Weight:290.31

23499-01-6 Synthesis

23499-01-6
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Ethyl (triphenylphosphoranylidene)acetate

1099-45-2
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ETHYL 2-[1-(4-NITROPHENYL)-4-PIPERIDINYLIDENE]ACETATE

251310-52-8
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Yield:251310-52-8 82%

Reaction Conditions:

in benzene; for 24 h;Product distribution / selectivity;Heating / reflux;

Steps:

Scheme 4a ; PPh₃=CHCOOC₂H₅ Benzene; [00235] To anhydrous benzene (50 mL) was added 2 (1.32 g, 6 mmol) and Ph3P=CHCOOC2H5(4.18 g, 12 mmol). The reaction mixture was heated at reflux for 24 hours under an argon atmosphere. The reaction was cooled and the solvent removed under vacuum. The crude mixture was dissolved in ethyl acetate, concentrated, and chromatographed on silica gel using hexanes/ethyl acetate (8:3) to afford compound 3 (1.42g, 82%). The desired product is the first compound to be eluted from the column R_f ~ 0.7).¹H NMR (400 MHz, CDCl₃): δ 1.29 (t, 3H), 2.5 (d, 2H), 3.13 (t, 2H), 3.58 (m, 4H), 4.20 (q, 2H), 5.81 (s, IH), 6.79 (d, 2H), 8.13 (d, 2H). MALDI-TOF: 289, calcd 289.13.

References:

WO2008/130637,2008,A1 Location in patent:Page/Page column 32-33