Sodium Azide → HCID 178478884, compound

Participants

Reaction Conditions

Reaction Steps

5-[2-(3,4-Dichlorophenyl)-4-(4-hydroxy-4-phenyl-piperidino)butyroyl]-4-phenyl-(1H)-1,2,3-triazole. A suspension of sodium azide (38 mg) in N,N-dimethylformamide (1 mL) was treated dropwise with a solution of 4-(3,4-dichlorophenyl)-6-(4-hydroxy-4-phenyl-piperidino)-1-phenyl-1-hexyn-3-one (287 mg) in N,N-dimethylformamide (4 mL). The reaction mixture was warmed to 35° C. and was stirred for 3 hours. The reaction was quenched by addition of water and extracted with ethyl acetate. The organic extracts were combined, washed (water, brine) and evaporated to leave an orange syrup. The syrup was triturated with dichloromethane to afford the triazole as a pale tan powder (260 mg, 83%). NMR (d6-DMSO): 7.89 (m, 2), 7.63 (d, J=1.8 Hz, 1), 7.57 (d, J=8.3 Hz, 1), 7.45-7.17 (m,9), 5.24 (t, J=7.3 Hz, 1H, H-C(2')), 4.91 (broad s, 1H, O), 2.86-2.50 (m,7), 1.95-1.49 (m,5H).

Provenance & Evidence