Diisopropyl Ether → HCID 69904074, compound

Participants

Reaction Steps

To a solution of (2S*,3S*,5R*)-5-hydroxymethyl-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-2-phenylpiperidine (0.298 g, 0.726 mmol) in EtOH (3.0 ml) was added fumaric acid (0.169 g, 1.45 mmol) in one portion. An additional volume of EtOH was added with heating at reflux, until the mixture became homogeneous. After the resultant pale yellow solution was allowed to cool to room temperature, (i-Pr)2O (2.0 ml) was added. After the mixture was left to stand in a refrigerator (at 4 C.) overnight, and then the precipitated white solids were collected by filtration, washed with (i-Pr)2O-i-PrOH, and dried in vacuo with heating at 50 C. to give title difumarete (0.382 g, 82.1%) as white powders. ##STR12## mp 162.0-165.0 C.; IRmax (nujol): 2565(br., s), 17179s), 1705(s), 1641(s), 1630(s), 1561(s), 1502(s), 1280(s), 1250(s), 1162(s), 973(s), 790(m), 751(s), 648(s) cm-1 ; 1H-NMR δ (DMSO-d6): 7.45-7.33(m, 4H), 7.22-7.12(m, 1H), 7.18-7.11(m, 2H), 6.91(d, J=8.8 Hz, 1H), 6.54(s, 4H), 4.29(br.s, 1H), 3.88-3.13(m, 13H), 3.56(s, 3H, 3.06-2.96(m, 1H), 2.90-2.83(m, 1H), 2.07-1.95(m, 1H), 1.93-1.80(m, 1H) ppm.

Provenance & Evidence