Acetyl chloride → HCID 25019287, compound

Participants

Reaction Steps

A solution of compound 1-amino-3-[2-(4-methoxy-phenyl)ethyl]-4-(3,4-dimethylphenyl)-2-imidazolidinone hydrochloride (300 mg, 0.80 mmol) in dichloromethane (3.0 mL) is cooled in an ice bath and triethylamine (0.26 mL, 1.8 mmol) is added, followed by dropwise addition of acetyl chloride (0.068 mL, 0.96 mmol). The reaction is stirred in the cold for 45 minutes and washed with 0.1 N aqueous HCl, H2O, 10% aqueous NaHCO3, and brine. The organic phase is dried (Na2SO4) and concentrated under reduced pressure. The residue is purified over silica (2.5% methanol/dichloromethane) to afford 237 mg (78% yield) of the desired compound. 1H NMR (CDCl3) δ 9.18 (s, 1H), 7.12 (m, 3H), 7.07 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.4 Hz), 4.41 (t, J=8.4 Hz, 1H), 3.91 (t, J=8.4 Hz, 1H), 3.81 (s, 3H), 3.71 (m, 1H), 3.59 (t, J=8.1 Hz, 1H), 2.94 (m, 1H), 2.80 (m, 1H), 2.67 (m, 1H), 2.29 (s, 6H), 2.09 (s, 3H). MS 382 (MH+). Anal. Calcd. For C22H27N3O3 ¼H2O: C, 68.46; H, 7.18; N, 10.89. Found: C, 68.72; H, 6.97; N, 10.85.

Provenance & Evidence