Dimethylamine → 4-(2-Chlorophenyl)-8-[3-(dimethylamino)propoxy]-9-methoxy-1h-[1]benzofuro[3,2-e]isoindole-1,3(2h)-dione

Participants

Reaction Steps

Reaction of dibromide (331) (100 mg, 0.16 mmol) prepared as described in example 385 with aqueous dimethylamine solution (40%, 5.0 mL) according to The procedure described in example 179, except that the reaction was performed in tetrahydrofuran (50 mL) at room temperature for 30 hours, gave the crude diamine (LXXX; Ar=2-chlorophenyl, n=3, Z═N(CH3)2), which was used without further purification as a tetrahydrofuran solution. To this solution was added SN potassium hydroxide (2.5 mL), then the procedure outlined in example 328 was followed except that the HCl treatment was for 24 hours and the chromatography was performed eluting with methanol/dichloromethane/concentrated ammonia (15:85:trace). Trituration from ethyl acetate gave amine (332) (64 mg, 84%) as a yellow powder, mp 251–253° C. 1H NMR δ [(CD3)2SO] 11.37 (br s, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 7.59 (m, 1H), 7.55 (s, 1H), 7.52–7.43 (m, 3H), 4.18 (t, J=6.4 Hz, 2H),3.93 (s, 3H), ˜2.5 (obscured m, 2H), 2.23 (br s, 6H), 1.96 (m, 2H). Found: C, 65.03; H, 4.79; N, 6.00. C26H23ClN2O5 requires: C, 65.21; H, 4.84; N, 5.85.

Provenance & Evidence