Dichloromethane → HCID 21258547, compound

Participants

Reaction Steps

A solution of the above protected tryptamine (2.1 g, in a mixture of dichloromethane and trifluoroacetic acid (1:1; 60 ml) was allowed to stand at room temperature for 3 h. The solvents were removed under vacuum and the residue was azeotroped with toluene-methanol (5:1; 100 ml). The residue was dissolved in 4N sodium hydroxide solution (50 ml) and extracted with ethyl acetate (3×100 ml). The combined organic solutions were washed with brine (1×50 ml), dried (Na2SO4) and concentrated. The hydrochloride salt was prepared and recrystallised from acetonitrile to give 1.53 g of the title compound; mp 117°-120° C.; δH (360 MHz, D2O) 7.81 (2H, d, J=7.5 Hz), 7.74 (1H, d, J=9.0 Hz), 7.56 (1H, s), 7.54 (1H, t, J=7.5 Hz), 7.41 (2H, t, J=8.1 Hz), 7.00 (1H, d, J=2.3 Hz), 6.89 (1H, dd, J=9.0 and 2.3 Hz), 6.89 (1H, dd, J=9.0 and 2.3 Hz), 3.78 (3H, s),3.29 (2H, t, J=7.6 Hz), 3.01 (2H, t, J=7.6 Hz); m/z (ES) 331 (M++1). (Found: C, 54.07; H, 5.39; N, 7.41. C17H18N2O3S.1.0HCl.0.6 H2O requires: C, 54.06; H, 5.39; N, 7.42%).

Provenance & Evidence