Methyl 3-[4-(aminomethyl)phenyl]propionate → Methyl 3-(4-{[(4-dec-1-ynylbenzyl)amino]methyl}phenyl)propanoate

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Reaction Steps

The title compound was prepared following the procedure A using 4-dec-1-ynylbenz-aldehyde and methyl 3-[4-(aminomethyl)phenyl]propanoate (purification by flash chromatography on SiO2, EtOAc/c-Hex 20/80) as a yellow oil (53%). 1H NMR (CDCl3) δ: 7.28 (d, J=8.3 Hz, 2H), 7.23-7.13 (m, 4H), 7.08 (d, J=7.9 Hz, 2H), 3.70 (s, 2H), 3.66 (s, 2H), 3.59 (s, 3H), 2.86 (t, J=8.3 Hz, 2H), 2.55 (t, J=7.2 Hz, 2H), 2.32 (t, J=7.2 Hz, 2H), 1.56-1.46 (m, 2H), 1.43-1.31 (m, 2H), 0.86-0.76 (m, 3H). M+ (ESI): 420.4. HPLC, Rt: 4.5 min (purity: 99.5%).

Provenance & Evidence