Potassium Hydroxide → HCID 69892198, compound

Participants

Reaction Conditions

Reaction Steps

0.4 ml of 1M potassium hydroxide solution were added to a solution of 80 mg (0.17 mmol) of methyl (E)-4-[[5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]methyl]benzoate in 8 ml of methanol. The mixture was heated at 60° C. for 4 hours then left at room temperature for 3 days. A further 0.2 ml of 1M potassium hydroxide solution were added followed by heating at 60° C. for 4 hours. The solvent was removed by evaporation and the residue dissolved in diethyl ether and water. The aqueous phase was separated, acidified with acetic acid and extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulphate, filtered and evaporated to dryness. The residue was chromatographed on silica gel using dichloromethane/methanol/acetic acid/water (120:15:3:2) for the elution. The product was dissolved in a mixture of 10 ml of acetone and 0.2 ml of concentrated hydrochloric acid, evaporated to dryness and the residue triturated with diethyl ether. There was obtained 55 mg of (E)-4-[[5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]methyl]benzoic acid dihydrochloride MS: m/e 451 [M+H]+.

Provenance & Evidence