Potassium Carbonate → HCID 22850906, 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 0.243 g (1.76 mmol) of anhydrous potassium carbonate and 0.310 ml (1.60 mmol) of 4-(tert-butyl)benzyl chloride. Chromatography on flash silica, eluting with 10-30% ethyl acetate/petroleum ether and 30-90% ether/petroleum ether, gave 0.142 g (27%) 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. 229°-230° C. (dec). NMR δ(D2O) 1.33 (9H, s), 1.52 (1H, m), 1.65 (1H, m), 1.72-1.84 (2H, m), 2.60-2.72 (2H, m), 2.88-2.94 (2H, m), 3.20 (1H, t of d), 3.51 (1H, m), 3.70 (1H, m), 4.33 (2H, m), 7.21-7.25 (3H, m), 7.30-7.32 (1H, m), 7.47 (2H, d, J=8.4 Hz), 7.61 (2H, d, J=8.3 Hz). m/z (CI+, NH3) 334 (M+H)+, 233, 186 (M-CH2C6H4CMe3)+, 113.

Provenance & Evidence