Hydrogen Bromide → HCID 20145262, compound

Participants

Reaction Steps

A solution of 0.072 gm (1.05 m mol) of sodium nitrite in 0.5 ml of water was added dropwise at an internal temperature of 0° to 5° C. to 0.40 gm (1.05 m mol) of 4-[(1-(5-amino-2-piperidino-phenyl)-ethyl)-aminocarbonylmethyl]-benzoic acid in 2 ml of semi-concentrated aqueous hydrobromic acid. The thus obtained diazonium salt solution was then added dropwise to 0.196 gm of copper-(I) bromide in 2 ml of 48% hydrobromic acid, whereby strong formation of gas occurred. The reaction mixture was stirred for 1.5 hours at an internal temperature of 45° to 50° C., cooled, and adjusted to pH 4 by means of 4N sodium hydroxide solution. After extraction with warm ethyl acetate, the extract was washed with water, dried, and filtered. After evaporation in vacuo, the residue obtained was purified by column chromatography on silica gel (chloroform/methanol=7:1).

Provenance & Evidence