Sodium Carbonate → HCID 46947043, compound

Participants

Reaction Conditions

Reaction Steps

5,7-Dichloro-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.36 g, 0.94 mmol), 4-hydroxypiperidine (0.38 g, 3.8 mmol), sodium carbonate (0.40 g, 3.8 mmol), and tetrabutylammonium iodide (0.09 g, 0.24 mmol) were combined in toluene (5 mL) and heated to 100° C. for 24 hours. The solution was cooled, diluted with ethyl acetate, washed with water, brine, dried with magnesium sulfate, filtered and concentrated in vacuo. Column chromatography eluting with a gradient of 25-100% ethyl acetate in hexanes provided 7-chloro-5-(4-hydroxypiperidin-1-yl)-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one. (35 mg, 8% yield) ESI m/z measured 448.1794 [M+H]+. calculated 448.1792.

Provenance & Evidence