Potassium Iodide → HCID 19879235, compound

Participants

Reaction Steps

A stirred solution of 1.2 g (2.7 mmoles) of 2-(4-hydroxyphenyl)-3 (4-pyridyl)-6,7-dihydro [5H]-pyrrolo[1,2-a]imidazole dihydrobromide of Example 10 in 20 ml of dry dimethylformamide cooled in an ice bath was treated with 360 mg (9.0 mmoles) of 60% sodium hydride dispersion and allowed to warm to room temperature. 450 mg (2.7 mmoles) of powdered potassium iodide was added, followed by dropwise addition of a solution of 332 mg (2.7 mmoles) of 1-propyl bromide in 2 ml of dimethylformamide. After 2 hours an additional 83 mg (0.67 mmole) of 1-propyl bromide was added followed by another 90 mg (2.25 mmoles) of 60% sodium hydride suspension, and the mixture heated to 65° C. for 2.5 hours. After stirring overnight, the mixture was poured into 10 volumes of ice water and extracted three times with ethyl acetate. The organic phase was washed with water, dried over anhydrous potassium carbonate and concentrated in vacuo. The residue was flash chromatographed on silica and the fractions eluting with 3 to 6% methanol in chloroform were combined, concentrated in vacuo, and recrystallized from ethyl acetate to afford the titled compound, mp 148.5-150° C. Anal. Calcd. for C20H21N3O: C, 75.21; H, 6.63; N, 13.16. Found: C, 4.95; H, 6.59; N, 13.17.

Provenance & Evidence