Pivaloyl chloride → 3-{N-[beta-(3,4-Dipivalyloxyphenyl)ethyl]}carbamoylpyridine

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Reaction Steps

To a suspension of 5.16 g (0.02 mol) finely powdered nicotinoyldopamine in 100 ml chloroform, 7.23 g (0.06 mol) trimethylacetyl chloride were added under stirring. The mixture was refluxed for 6 hours and then filtered. The filtrate was washed with water free of chloride ions, then washed once with a 5% solution of NaHCO3, then with water. The chloroform was evaporated and the residue was chromatographed by using a silica gel G column and 2% methanol in chloroform as the eluent. The first fraction was collected and evaporated and the residue was crystallized from ether/petroleum ether. Yield, 6.2 g (73%) of a white crystalline solid, m.p. 112°-114° C., NMR (CDCl3) δ9.06 (bs, 1H, C2 pyridine proton), 8.73 (bd, 1H, C6 pyridine proton) 8.30-8.13 (m, 1H, C4 pyridine proton), 7.46-7.10 (m, 5H, C6H3 +C5 pyridine proton+CONH), 3.66 (q, 2H, J=6.25 Hz, --N--CH2), 3.0 (t, 2H, J=6 Hz, --CH2), 1.41 [s, 18H, 2--C(CH3)3 ]. Anal. Calcd for C24H30N2O5 : C, 67,58; H, 7.09; N, 6.56. Found: C, 67.61; H, 7.10; N, 6.54.

Provenance & Evidence