1-Methylpiperazine → HCID 69318372, compound

Participants

Reaction Steps

10-[4-(2-Methyl-cyclohex-1-enyl)-benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid of Step F (0.0510 g, 0.120 mmol) and oxalyl chloride (0.011mL, 0.126 mmol) were combined in anhydrous dichloromethane (1.2 mL) followed by dropwise addition of N,N-dimethylformamide (0.0003 mL, 0.0036 mmol). The reaction was refluxed for 3 hours, then the solvent was removed and the residue dried in vacuo. The crude acid chloride thus prepared was combined with N-methylpiperazine (0.0146 mL, 0.132 mmol) and N,N-diisopropylethyl amine (0.025 mL, 0.144 mmol) in anhydrous dichloromethane (1.2 mL). After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with 5% methanol in chloroform to afford the title compound (0.025 g) as a white solid from a mixture of diethyl ether and hexane,

Provenance & Evidence