Tyramine → bis-(2-Chloroethyl)amino-4-hydroxyphenylaminomethanone

Participants

Reaction Steps

27 (860 mg, 2.8 mmol) was dissolved in dimethylformamide (20 mL) and triethylamine (0.9 mL, 5.6 mmol) was added. The mixture was stirred at reflux for 30 minutes and tyramine (0.76 mg, 5.6 mmol) was added. The mixture was heated under reflux for a further 6 hours and then concentrated in vacuo. Purification by column chromatography (silica gel, dichloromethane then methanol) gave prodrug 28 as an orange/brown oil (571 mg, 67%). νmax 3400, 1660, 1444, 1380, 1145/cm−1; δ 1H (400 MHz, CDCl3) 2.61 (2H, t, J 3.72 Hz, 4,CH2Ar), 3.17–3.22 (10H, m, ArCH2CH2, 2×CH2CH2Cl), 6.67 (2H, d, J 5.7 Hz, 2×ArH), 6.9 (2H, d, J 5.7 Hz, 2×ArH), 7.82 (1H, brs, NH); 13C (100 MHz, CDCl3), 30.1 (CH2), 43.1 (CH2), 43.4 (CH2), 44.2 (CH2), 46.2 (CH2), 46.7 (CH2), 115.9 (2×CH), 130 (2×CH), 130.1 (C), 155.6 (C), 161.5 (C). m/z (Cl) 269 (87%), 224 (50), 138 (100), 121 (45), 108 (35).

Provenance & Evidence