HCID 13472779, compound → HCID 13472846, compound

Participants

Reaction Steps

A suspension of the di(lower)alkoxy compound, 4,5-dimethoxy-2-methyl-1,2,3,7,8,12b-hexahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline (1.0 g, 3.2 mmol, described in example 4) in 58% (v/w) hydriodic acid (30 mL) was stirred in a closed vessel for 3 weeks at 20°-22° C. The reaction mixture was poured into ice water (50 mL). The resulting precipitate was collected, washed with a small amount of water, and then partitioned between concentrated ammonium hydroxide-water (1:1, v/v) and ethyl acetate. The organic phase was separated, washed with brine, dried (MgSO4) and evaporated to dryness to give the title compound as a yellow solid. The product was purified by converting it to its hydrochloride and then regenerating the free base (0.864 g) from the hydrochloride. When purified in this manner and recrystallized from chloroform-hexane, the title compound had mp 173°-174° C.; NMR (CDCl3) δ2.50 (s, 3H), 3.75 (s, 3H), 4.55 (m, 1H), 5.50 (broad, 1H), 6.34 (s, 1H), 7.10 (m, 3H), 7.50 (m, 1H); Anal Calcd for C19H21NO2 : C, 77.26% H, 7.17% N, 4.74%; Found: C, 77.36% H, 7.23% N, 4.68%.

Provenance & Evidence