Cyanoacetamide → Piperidine

Participants

Reaction Steps

From a solution of the sodium salt of p-(dimethylamino)benzoylacetaldehyde in 400 ml. of water (prepared from 11.4 g. of sodium methoxide in 100 ml. of tetrahydrofuran and a solution of 29.3 g. of p-(dimethylamino)acetophenone [J.A.C.S. 73, 864 (1951)] and 13.3 g. of ethyl formate in 130 ml. of tetrahydrofuran), 18.5 g. of 2-cyanoacetamide and a solution consisting of 2.3 ml. of acetic acid, 5.2 ml. of water and 4.0 ml. of piperidine, there is obtained 6-[p-(dimethylamino)phenyl]-1,2-dihydro-2-oxonicotinonitrile; m.p. 280°-292° (dec.) after crystallization from aqueous dimethyl sulfoxide.

Provenance & Evidence