Formaldehyde → HCID 59395953, compound

Participants

Reaction Steps

To a solution of (2R)-2-(N-Methylamino)-3-phenyl-1-(4-quinazolin-4-yl-piperazin-1-yl)-propan-1-one (free-base, 14 mg, 0.037 mmol) in 1,2-dichloroethane was added a solution of formaldehyde (37% w/w, 50 μL, 0.61 mmol) and then Na(OAc)3BH (0.12 mmol). The reaction mixture was stirred at room temperature for 3 hours, after which saturated NaHCO3 was added, and the reaction mixture was stirred 10 minutes. The suspension was extracted with DCM, and the combined extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation. The residue was filtered through a Fluorosil plug with ETOAC, and the filtrate was concentrated by rotary evaporation. The resulting residue was dissolved in ether and excess 4M HCl/dioxane was added. The yellow solids were isolated by filtration with nitrogen pressure and dried under reduced pressure to afford the desired product (7 mg, 41%) as the dihydrochloride salt. Rt 2.20. MS (ESI+) [M+H]+ 390.

Provenance & Evidence