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

Participants

Reaction Steps

To an ice cold suspension of 4.84 g (0.02 mol) N-nicotinoyltyramine in 100 ml chloroform, 3.6 g (0.03 mol) of trimethylacetyl chloride were dropped while stirring. The mixture was refluxed overnight and the non-reacted nicotinoyltyramine was filtered off. The filtrate was washed with water until free from chloride ions, washed once with 5% solution of NaHCO3 and then with water. Chloroform was evaporated on rotavap and the residue was crystallized from ether/pet. ether. Yield 3.9 g (60%), m.p. 80°-82° C. PMR (CDCl3) δ 8.66-6.93 (m, 8H, C5H4N+C6H4), 3.56 ##STR741## 2.86 (5, 2H, J=7 Hz, CH2), 1.33 (s, 9H, C--(CH3)3).

Provenance & Evidence