Formaldehyde → HCID 19367098, compound

Participants

Reaction Steps

A mixture of 6-chloro-2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]-methyl]imidazo[1,2-a]pyridine (Example 31, Step 2; 0.125 g), 37% formaldehyde in water (2 mL), and THF (2 mL) is stirred at 85° C. for 50 min, at which time an additional 1 mL of 37% formaldehyde in water is added. A third addition of 37% formaldehyde in water (1 mL) is made 1.5 h later. After the mixture has stirred for a total of 22 h, the heat is turned off and the mixture is allowed to stir at room temperature an additional 12 h. The mixture is then partitioned between dichloromethane and aq. sodium bicarbonate. Chromatography on silica gel using methanol/dichloromethane (3/97) gives 0.132 g of product, which after crystallization from dichloromethane/hexane gives 0.125 g of the title compound; mp 165-166° C.; MS m/z 424, 426; IR (mineral oil) 1479, 792, 1021, 816, 1502 cm-1. 1H NMR (CDCl3) δ2.79, 3.05, 3.90, 4.93, 6.1, 6.92, 7.17, 7.35, 7.52, 8.04.

Provenance & Evidence