Acetic Acid → HCID 131722451, compound

Participants

Reaction Steps

Sodium cyanoborohydride (1.59 g, 25.3 mmol) was added to a solution of naphthalenone 7 (3.00 g, 12.7 mmol), tryptamine (2.03 g, 12.7 mmol), and acetic acid (0.76 g, 12.7 mmol) in methanol (100 mL). The reaction mixture was stirred for 20 h under nitrogen and then concentrated in vacuo to provide an orange-yellow solid. Saturated aqueous sodium carbonate solution was added to this residue, and the resulting mixture was extracted with chloroform. The chloroform extracts were combined, dried (Na2SO4), and concentrated to provide an orange-brown foam which was purified on flash silica gel (10% hexanes-chloroform to 1% methanol-chloroform) to provide the desired product as a red-beige foam. This material was dissolved in a minimum amount of acetone, and fumaric acid (0.84 g) was added. Diethyl ether and hexanes were added to precipitate a cream-colored solid and this material was crystallized from methanol to give 1.75 g (31%) of rac-cis-1-(phenylmethyl)-6-methoxy-N-(2-(3-indolyl)ethyl)-1,2,3,4-tetrahydro-2-naphthalenamine hemifumarate 8 (FIG. 4). mp 241.5-244.5° C. MS (PB-CH4), m/z 381 (MH+). 1H NMR (DMSO-d6) 1.80-2.00 (m, 2H), 2.40-2.50 (m 1H), 2.78-2.90 (m, 1H), 2.88-3.24 (m, 9H), 6.27 (d, J=7.7 Hz, 1H), 6.54 (s, 1H), 6.80 (br t, J=7.1 Hz, 1H), 6.88-7.28 (m, 11H), 7.35 (d, J=6.9 Hz, 1H), 7.57 (d, J=7.7 Hz, 1 H), 10.88 (br s, 1H).

Provenance & Evidence