Sodium Cyanide → HCID 13019462, compound

Participants

Reaction Steps

A solution of sodium nitrite (0.3 g) in water (5 ml) was added dropwise to a stirred solution of 3-(4-aminophenyl)-N,N-dimethyl-3-(imidazol-2-yl) propanamine (1.0 g) in 2 N hydrochloric acid (6 ml) and water (6 ml), keeping the temperature at 3°-5°. After stirring for 30 min. the dark red solution was adjusted to pH 7-8 and treated with sodium cyanide (0.2 g) and cuprous cyanide (0.4 g) and heated on a steam bath for 3 h. The mixture was then adjusted to pH 11-12 and extracted with ethyl acetate (3×30 ml). The extracts were dried (Na2SO4) and concentrated to give the title compound as a gum (0.33 g) which was taken up into methanol (5 ml) and treated with a solution of maleic acid (0.15 g) in methanol (5 ml). Removal of the solvent and trituration of the residue with ether gave the dimaleate salt of the title compound as an off white solid that crystallised from ethanol-ether with m.p. 147°-148°; τ(D2O)2.06 to 2.35 (2H,m,aromatic),2.48(2H,br.s,imidazole), ##STR36## 6.5-7.5(4H,m,CH2CH2N(CH3)2),7.03(6H,s,N(CH3)2).

Provenance & Evidence