1-(2,4-Dichlorobenzyl)piperazine → 1-{2-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpiperidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2,4-dichlorobenzyl)piperazine (0.415 g, 1.693 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.498 g, 1.608 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.389 g, 2.031 mmol) were stirred together in dichloroethane (0.5 mL) at room temperature for 2 hours. The reaction was then heated to 85° C. and stirred overnight. The reaction was cooled, loaded onto a SF25-40 column (Analogix®) and the product eluted using a gradient of 5% ethyl acetate/hexanes to 100% ethyl acetate over 30 minutes, then holding at 100% ethyl acetate for 15 minutes (Flow=45 mL/minute) to yield the title compound. 1H NMR (300 MHz, CDCl3) δ 7.42-7.36 (m, 2H), 7.32 (s, 11H), 4.23 (s, 2H), 3.65 (s, 2H), 3.57 (s, 2H), 3.49 (dd, J=6.5, 13.6, 4H), 2.72-2.56 (m, 2H), 2.48 (s, 4H), 1.94-1.74 (m, 2H); MS (ESI+) m/z 536.1 (M+H)+.

Provenance & Evidence