Potassium Carbonate → HCID 22850901, compound

Participants

Reaction Steps

Following the procedure of Example 3, step 4, 0.300 g (1.60 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.244 g (1.77 mmol) of anhydrous potassium carbonate and 0.369 g (1.60 mmol) of 4-nitrophenethyl bromide. Chromatography on flash silica, eluting with 50-100% ethyl acetate/petroleum ether, then on a Lobar column, eluting with 50% ethyl acetate/petroleum ether, afforded 0.200 g (37%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent the title product hydrochloride was obtained as a white solid, m.p. 232°-233° C. (dec). NMR δ(CDCl3) 1.50 (1H, m), 1.86-1.91 (1H, m), 2.28-2.61 (5H, m), 2.86-3.06 (3H, m), 3.24-3.26 (2H, m), 3.49-3.52 (2H, m), 3.66 (1H, m), 3.85 (1H, m), 7.10-7.19 (4H, m), 7.49 (2H, d, J=8.6 Hz), 8.19 (2H, d, J=8.6 Hz). m/z (CI+, NH3) 307 (M-NO+H)+, 200 (M-CH2C6H4NO2)+, 188.

Provenance & Evidence