1-Isopropylpiperazine → HCID 10144266, compound

Participants

Reaction Conditions

Reaction Steps

To a dry flask charged with anhydrous CH2Cl2 (1 mL) was added 1-isopropylpiperazine (0.057 mL, 0.434 mmol, 2 eq). The mixture was cooled to 0° C. under nitrogen. To this cooled mixture was added Al(CH3)3 (0.217 mL of a 2M toluene solution, 0.434 mmol, 2 eq). After 15 min, methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,4-dihydro-2H-3,1-benzoxazine-7-carboxylate (100 mg, 0.217 mmol, 1 eq) was dissolved in CH2Cl2 (1 mL) and added to the aluminum reagent at 0° C. under nitrogen. After 2 min the cooling bath was removed. Let stir at rt for 5d. The reaction was diluted with CH2Cl2, and washed with water. The aqueous layer was back extracted 2× with CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated. The product was purified by flash column chromatography on silica gel eluting with 2:1 hexanes/acetone giving 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(4-isopropylpiperazin-1-yl)carbonyl]-1,4-dihydro-2H-3,1-benzoxazin-2-one. Mass spectrum (ESI) 458.0 (M+1); 460 (M+3).

Provenance & Evidence