Benzhydrylpiperazine → HCID 53386258, compound

Participants

Reaction Steps

To a solution of 1-benzhydrylpiperazine (1.63 g, 6.46 mmol) in dichloromethane (75 mL) under nitrogen was added the product of Example 68E (2.00 g, 6.46 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (2.48 g, 12.93 mmol) and N,N-dimethylpyridin-4-amine (0.079 g, 0.65 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2, 400 mL). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (1:3) gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.38-7.42 (m, 4H), 7.25-7.31 (m, 12H), 7.16-7.24 (m, 4H), 4.23 (s, 1H), 4.20 (s, 2H), 3.64 (t, J=4.7 Hz, 2H), 3.47 (t, J=6.5 Hz, 2H), 3.41-3.45 (m, 2H), 2.60-2.65 (m, 2H), 2.34-2.42 (m, 4H), 1.78-1.87 (m, 2H); MS (DCI+) m/z 544 (M+H)+.

Provenance & Evidence