1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 135883266, compound

Participants

Reaction Conditions

Reaction Steps

(Z)—N′,4-Dihydroxybenzimidamide (0.251 g, 1.649 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.510 g, 1.649 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.474 g, 2.473 mmol) were stirred together in dichloroethane at room temperature for 2 hours, then heated to 85° C. for 16 hours. The reaction was cooled and concentrated. The residue was dissolved in dichloromethane (5 mL) and washed with water (3 mL). The organic layer was concentrated and the residue was loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 35% ethyl acetate/hexanes (Flow=35 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.95-7.78 (m, 2H), 7.40-7.16 (m, 10H), 6.85-6.71 (m, 2H), 5.93 (s, 1H), 4.88 (s, 2H), 3.64 (t, J=6.5, 2H), 2.78-2.66 (m, 2H), 1.99-1.80 (m, 2H); MS (ESI+) m/z 426.1 (M+H)+.

Provenance & Evidence