4.1.23. 1-(4-Bromophenoxy)-3-(dibenzylamino)propan-2-ol (21)

Following the general procedure, dibenzylamine (CAS 103-49-1) (0.42 mL, 2.21 mmol) and 2-[(4-bromophenoxy)methyl]oxirane (500 mg, 2.18 mmol) afforded 21 (800 mg, 86%) as a white solid after column chromatography (hexane/EtOAc 9:1 to 8:2). Mp 63–65 °C (EtOAc). IR (ATR) 3568, 3413, 3031, 2936, 1587, 1488, 1243, 1036, 830, 804, 744, 733, 698 cm⁻¹. ¹H NMR (500 MHz, CDCl₃, HETCOR) δ 2.66 (d, J = 7.0 Hz, 2H, CH₂N), 3.19 (s, 1H, OH), 3.54 (d, J = 13.5 Hz, 2H, CH₂Ph), 3.80 (d, J = 13.5 Hz, 2H, CH₂Ph), 3.83 (m, 2H, CH₂O), 4.03–4.14 (m, 1H, CH), 6.68–6.74 (m, 2H, ArH), 7.23–7.30 (m, 2H, ArH), 7.30–7.42 (m, 10H, ArH). ¹³C NMR (101 MHz, CDCl₃) δ 56.1 (CH₂N), 58.9 (2CH₂Ph), 66.5 (CH), 70.7 (CH₂O), 113.2 (CAr), 116.5 (2CHAr), 127.5 (2CHAr), 128.6 (4CHAr), 129.2 (4CHAr), 132.3 (2CHAr), 138.6 (2CAr), 157.9 (OCAr). HRMS C₂₃H₂₅BrNO₂ [M + H]⁺ 426.1063; found 426.1064. Purity 97.85% (t_R = 4.17 min).