Nitrogen → HCID 44213309, compound

Participants

Reaction Steps

1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole (1.50 g, 8.7 mmol) was suspended in methyl isobutyl ketone (50 ml). 1-(2-Chloroethyl)-1,3-dihydro-2H-benzimidazol-2-one (1.958 g, 9.58 mmol) was added to the mixture along with sodium carbonate (1.110 g, 10.45 mmol) and tetrabutyl ammonium iodide (10 mg). The suspension was heated to 90° C. for 2 days, under an inert (N2) atmosphere. The mixture was concentrated in vacuo to dryness. Water (70 ml) was added, followed by addition of 2N HCl to pH1. The mixture was extracted with CHCl3 (2×70 ml), basified to pH10 using 5N NaOH, and again extracted with CHCl3 (3×70 ml). The organics were combined and washed with brine, separated and dried over MgSO4. The resulting solid was purified by chromatography (CHCl3, MeOH (2%)) to yield a yellow solid, m.p. 214°-216° C.

Provenance & Evidence