Sodium Hydroxide → HCID 68557074, compound

Participants

Reaction Steps

A sample of ethyl 2-(1-(4-chloro-3-methoxyphenyl)piperidin-4-yl)propanoate (130 mg, 0.359 mmol) was suspended in glacial AcOH (4 mL) and water (0.5 mL). The resultant solution was treated with N-chlorosuccinimide (62.3 mg, 0.467 mmol) and then stirred at RT overnight. After this time, the mixture was diluted with water (10 mL) and Et2O (25 mL) and the pH was adjusted to pH 9 using 6 M NaOH (aq). The phases were separated and the aqueous phase was extracted with Et2O. The extracts were combined, washed with brine, dried (MgSO4) and concentrated on a rotary evaporator. The resultant residue was purified by flash chromatography using a 12 g silica gel cartridge and gradient elution from 10:1 Hex/EtOAc to 5:1 Hex/EtOAc. The fractions containing the product were pooled and concentrated on a rotary evaporator to give ethyl 2-(1-(2,4-dichloro-5-methoxyphenyl)piperidin-4-yl)propanoate (80 mg, 0.222 mmol, 62% yield) as an oil. 1H-NMR (500 MHz, CDCl3) δ ppm 7.32 (1 H, s), 6.58 (1 H, s), 4.15 (2 H, qd, J=7.06, 1.92 Hz), 3.87 (3 H, s), 3.34-3.41 (2 H, m), 2.60 (2 H, t, J=11.55 Hz), 2.33 (1 H, dt, J=14.30, 7.15 Hz), 1.81 (1 H, dt, J=12.92, 2.61 Hz), 1.65-1.73 (2 H, m), 1.44-1.62 (2 H, m), 1.27 (3 H, t, J=7.15 Hz), 1.16 (3 H, d, J=7.15 Hz). LC-MS: 360, [M+H]; tR=4.28 min (method b).

Provenance & Evidence