Chloroform → HCID 69185047, compound

Participants

Reaction Steps

10-[2-(4-amino-1-piperidinyl)ethyl]-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-9(10H)-one (100 mg; 0.304 mmol) and 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxaldehyde (for a synthesis see WO2004058144, Example 2(c) or WO03/087098, Example 19(d)) (50 mg; 0.304 mmol) were dissolved in a 5:1 mixture of chloroform and MeOH (5 ml:1 ml) and stirred at rt for 2.5 h. More 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (10 mg; 0.031 mmol) was added to the reaction and stirred for 20 mins. This was then treated with NaBH(OAc)3 (20 mg; 0.092 mmol) and stirred for 30 mins. More 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (10 mg; 0.031 mmol) was added to the reaction and stirred for 15 mins. This was then treated with NaBH(OAc)3 (20 mg; 0.092 mmol) and stirred for 15 mins. The solvents were then removed and the crude residues purified by column chromatography on silica gel using a 0-20% 2M NH3:MeOH/DCM gradient. Fractions containing the desired were concentrated to afford the free base of the title compound. (140 mg; 96%). δH CDCl3, (400 MHz) 1.49 (m, 2H), 1.8-2.6 (m, 8H), 2.76 (m, 2H), 3.04 (d, 2H), 3.81 (s, 2H), 4.2-4.4 (m, 8H), 4.71 (m, 2H), 6.51 (d, 1H), 6.78 (d, 1H), 6.83 (s, 1H), 7.01 (d, 1H), 7.49 (d, 1H), 8.1 (s, 1H).

Provenance & Evidence