Chlorambucil → Methyl 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate

Participants

Reaction Steps

A mixture of chlorambucil (600 mg, 2 mmol), HBTO (625 mg, 2 mmol), and N,N-diisopropylethylamine (300 uL, 2 mmol) was stirred in methanol at 55° C. for 18 hrs. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 50 mL water. The mixture was then extracted with EtOAc and the combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/CH2Cl2 (10:1) to provide the compound 27a (350 mg, 1.1 mmol, 55% yield) as a yellow oil. 1H NMR (400 MHz, Chloroform-d) δ 7.20-7.05 (dd, 2H), 6.71-6.62 (dd, 2H), 3.75-3.70 (m, 4H), 3.69 (s, 3H), 3.64 (m, 4H), 2.58 (t, J=7.6 Hz, 2H), 2.35 (t, J=7.5 Hz, 2H), 1.93 (p, J=7.6 Hz, 2H). HRMS (ESI, positive) m/z calcd. for C15H22Cl2NO2 [M+H]+: 318.10221, found: 318.10216.

Provenance & Evidence