1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57396817, compound

Participants

Reaction Steps

To a solution of 4,4-diphenylpiperidine (Matrix, 0.24 g, 1.00 mmol) in dichloromethane (20 mL) was added 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.308 g, 1.00 mmol), under nitrogen. To the reaction was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.38 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (0.012 g, 0.10 mmol), and the reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate:water (8:2). The organic layer was separated, washed with water and then brine, dried over MgSO4, filtered and concentrated. Silica gel chromatography eluting with 3% methanol/dichloromethane gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.15-7.34 (m, 20H), 4.23 (s, 2H), 3.68-3.73 (m, 2H), 3.45-3.52 (m, 4H), 2.60-2.66 (m, 2H), 2.37-2.45 (m, 4H), 1.78-1.88 (m, 2H); MS (DCI+) m/z 529 (M+H)+.

Provenance & Evidence