Chloromethyl Methyl Ether → 1-[4-(Methoxymethoxy)phenyl]-4-(4-nitrophenyl)piperazine

Participants

Reaction Steps

To a mixture of 10 (263.4 mg, 0.88 mmol) and diisopropylamine (DIPEA) (170.6 mg, 1.32 mmol) in CH2Cl2 (12 mL) was added slowly chloromethyl methyl ether (77.9 mg, 0.97 mmol) at room temperature. The reaction was stirred for 16 h, and then quenched by the addition of saturated aqueous ammonium chloride (10 mL). The resulting solution was extracted with more CH2O2, dried (Na2SO4), filtered, and concentrated to yield the crude product, which was purified by column chromatography (neat CH2Cl2→100:1 CH2Cl2-Acetone) to afford 11 (250.8 mg, 83%) as a yellow amorphous solid; 1H NMR (400 MHz, CDCl3, δH) 8.20-8.08 (m, 2H), 7.07-6.97 (m, 2H), 6.97-6.82 (m, 4H), 5.13 (s, 2H), 3.62-3.51 (m, 4H), 3.48 (s, 3H), 3.30-3.18 (m, 4H); 13C NMR (100 MHz, CDCl3, δC) 154.99, 151.98, 146.31, 138.84, 126.18, 118.59, 117.58, 113.04, 95.28, 56.13, 50.42, 47.43. MALDI-MS: 344.2 (M+H+), 366.2 (M+Na+).

Provenance & Evidence