Ethylenediamine → 4-[(5R*,6S*)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3-diazaspiro[4.4]non-6-yl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (1 g, 2.1 mmol) (Example 1) and CuCN (0.45 g, 5 mmol) in NMP was heated to 180° C. for 6 h. After cooling, the reaction mixture was poured on a mixture of ice and ethylene diamine and extracted twice with DCM. The brown residue was chromatographed over silica gel to yield 4-[(5R*,6S*)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3-diazaspiro[4.4] non-6-yl]benzonitrile as a beige solid. 1H NMR (CDCl3): 7.62 (2H, d, J=8.1 Hz), 7.25–7.3 (3H, m), 6.67 (2H, br s), 3.45 (1H, dd, J1=12.8 Hz, J2=6.4 Hz), 3.16 (3H, s), 2.4–2.7 (1H, m), 1.8–2.4 (5H, m).

Provenance & Evidence