Potassium Iodide → HCID 18469945, compound

Participants

Reaction Steps

Under nitrogen atmosphere, a 3-necked 500 ml round-bottomed flask was charged with homopiperazine (20 mg), DMF (130 ml) and potassium iodide (0.35 g). A solution of 7.70 g (41.7 mmol) of 1-chloro-6-fluoro-1,2,3,4-tetrahydronaphthalene in 39 ml of DMF was added over a five minute period. The mixture was stirred at 55°-60° C. for two hours and then at ambient temperature overnight. Tlc analysis on silica gel (diethyl ether:hexane 5:95) showed the absence of the starting halide, Rf 0.77. Most of the DMF was then removed in vacuo (35° C., 0.6 torr) using a rotary evaporator. The residue was treated with 300 ml of water and extracted with ethyl acetate which was then dried (MgSO4). Filtration and removal of solvent in vacuo gave a yellow oil which was kugelrohr distilled to give the title compound, (8.63 g), bp (air bath temperature) 155°-166° C. at 0.26 torr, as a viscous yellow oil. 1H NMR (300 MHz, CDCl3) δ 3.86 (t, 1H, ArCHN), 6.78 (dd, 1H), 6.85 (m, 1H), 7.75 (m, 1H). Anal: Calcd. for C15H21FN2: C, 72.55; H, 8.52; N, 11.28. Found: C, 72.05; H, 8.53; N. 10.95. 1-Chloro-6-fluoro-1,2,3,4-tetrahydronaphthalene was prepared as follows:

Provenance & Evidence