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

Participants

Reaction Steps

To a suspension of 5.16 g (0.02 mol) finely powdered nicotinoyldopamine in 100 ml of chloroform, 7.23 g (0.06 mol) trimethylacetyl chloride was dropped while stirring. The mixture was refluxed for 6 hrs and then filtered. The filtrate was washed with water until free of chloride ions, then washed once with 5% solution of NaHCO3 then with water. Chloroform was distilled off on rotavap and the residue was chromatographed using silica gel G column and 2% methanol in chloroform as the elution solvent. The first fraction was collected, evaporated and the residue was crystallized from ether/pet. ether. Yield 6.2 g (78%) of white crystalline solid, m.p. 112°-114° C., PMR (CDCl3) 9.06 (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, ##STR35## 3.0 (t, 2H, J=6.5 Hz, --CH2), 1.41 (s, 18H, 2--C--(CH3)3). Anal. (C24H30N2O5) C, H, N.

Provenance & Evidence