4-Methylmorpholine → HCID 23289893, compound

Participants

Reaction Conditions

Reaction Steps

(8-Chloro-6,11-dihydro-6-methyl-5H-pyrido[3,2-c][1]benzazepin-11-yl)-piperazine (531 mg, 1.14 mmol), 1-(1,1-dimethylethoxycarbonyl)-4-piperidine-acetic acid (570 mg, 2.3 mmol), EDCl (439 mg) and HOBT (311mg) were dissolved in DMF (8 ml), and NMM (4 ml) was added. The reaction mixture was stirred at 20° C. for 20 hours and then water (100 ml) was added, and the resulting tan suspension was extracted with EtOAc (2×30 ml). The EtOAc phase was then washed with Na2CO3 (30 ml), dried over Na2SO4, filtered, and evaporated. The product was chromatographed over silica gel in CH2Cl2, and the column was eluted with CH2Cl2 and with CH2Cl2 /MeOH (95:5). The resulting purer material (0.75 g) was rechromatographed over silica gel in hexane/acetone (85:15) and eluted with increasing amounts of acetone (finally 30%). The product was rechromatographed on silica gel to afford the title compound (0.19 g), m.p. 86-98° C.; found: C, 64.64; H, 7.39; N, 12.12; calcd. for C30H40ClN5O3 : C, 65.03; H, 7.28; N, 12.64; HRMS: calcd. 554.2898; found 554.2891.

Provenance & Evidence