Triethylamine → HCID 21023601, compound

Participants

Reaction Steps

To a solution of (hydroxyimino)(4-methylphenyl)methane (97 mg, 0.72 mmol) in 1 ml of dichloromethane was added aqueous sodium hypochlorite solution (>4%, 1.33 ml, 0.72 mmol). The reaction mixture was stirred at room temperature for 30 minutes, after which time TLC (20:1 dichloromethane:methanol) showed conversion of oxime to chlorinated oxime (17). 1-(2-Methylbenzothiazol-5-yloxy)-3-(4-prop-2-enylpiperazinyl)propan-2-ol (50 mg, 0.144 mmol) in 0.5 ml of dichloromethane and triethylamine (0.022 ml, 0.145 mmol) were added. The reaction was stirred at room temperature overnight. Thin layer chromatography (10:1 dichloromethane:methanol) showed consumption of starting material and product formation. The solution was evaporated under reduced pressure, and the residue purified by preperative HPLC, to yield (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-{[3-(4-methylphenyl)(4,5-dihydroisoxazol-5-yl)]methyl}piperazinyl)propan-2-ol (3.6 mg, M+1=481.35)

Provenance & Evidence