Methanol → 3-(9-Phenylxanthen-9-yl)aminopropyne

Participants

Reaction Steps

9-Chloro-9-phenylxanthen (14.7 g, 50 mmol) was added in two equal portions over 0.5 h to a stirred solution of 3-aminopropyne (8.6 mL, 125 mmol) in DMF (100 mL). After 3 h, MeOH (20 mL) was added and the reaction mixture was stirred for 15 min. The mixture was then extracted into diethyl ether (500 mL) and washed with H2O (3×300 mL), dried (Na2SO4), and the solvent removed under vacuum. The resulting yellow oil was dried under high vacuum (4 h), and then redissolved in hot diethyl ether (70 mL). The solution was kept at -20° C. for 24 h and then filtered, the solid washed with ice-cold hexand (2×50 mL) followed by ice-cold diethyl ether (2×50 mL), giving 12 as a colourless powder (12.7 g, 82%), mp 116-8° C. 1H NMR (d6 -DMSO): δ2.86 (dd, 2H, H3, J=7.3, 4.4 Hz), 2.99 (t, 1H, H1, J=2.4 Hz), 4.01 (t, 1H, NH, J=7.2 Hz), 6.98-7.50 (m, 13H, Px CH). 13C NMR (d6 -DMSO): δ32.8 (C3), 59.7 (Px C9), 73.4 (C1), 82.7 (C2), 1160.0 and 123.5 (Px CH), 125.0 (Px C8a and C9a), 126.3, 126.4, 128.0, 128.6, 128.7 (Px CH), 149.5 (Px C1'), 150.7 (Px C4a and C10a). FABMS m/z 311 (M+). Anal. calcd for C22H17NO: C, 84.8; H, 5.51; N,4.50. Found: C, 84.4; H. 5.73; N, 4.30.

Provenance & Evidence